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[ CAS No. 14618-80-5 ] {[proInfo.proName]}

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Chemical Structure| 14618-80-5
Chemical Structure| 14618-80-5
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Product Details of [ 14618-80-5 ]

CAS No. :14618-80-5 MDL No. :MFCD00068409
Formula : C10H12O2 Boiling Point : -
Linear Structure Formula :- InChI Key :QNYBOILAKBSWFG-JTQLQIEISA-N
M.W : 164.20 Pubchem ID :159746
Synonyms :

Calculated chemistry of [ 14618-80-5 ]      Expand+

Physicochemical Properties

Num. heavy atoms : 12
Num. arom. heavy atoms : 6
Fraction Csp3 : 0.4
Num. rotatable bonds : 4
Num. H-bond acceptors : 2.0
Num. H-bond donors : 0.0
Molar Refractivity : 45.88
TPSA : 21.76 ?2

Pharmacokinetics

GI absorption : High
BBB permeant : Yes
P-gp substrate : No
CYP1A2 inhibitor : No
CYP2C19 inhibitor : No
CYP2C9 inhibitor : No
CYP2D6 inhibitor : No
CYP3A4 inhibitor : No
Log Kp (skin permeation) : -6.4 cm/s

Lipophilicity

Log Po/w (iLOGP) : 2.4
Log Po/w (XLOGP3) : 1.27
Log Po/w (WLOGP) : 1.45
Log Po/w (MLOGP) : 1.17
Log Po/w (SILICOS-IT) : 2.75
Consensus Log Po/w : 1.81

Druglikeness

Lipinski : 0.0
Ghose : None
Veber : 0.0
Egan : 0.0
Muegge : 1.0
Bioavailability Score : 0.55

Water Solubility

Log S (ESOL) : -1.76
Solubility : 2.83 mg/ml ; 0.0172 mol/l
Class : Very soluble
Log S (Ali) : -1.33
Solubility : 7.75 mg/ml ; 0.0472 mol/l
Class : Very soluble
Log S (SILICOS-IT) : -3.0
Solubility : 0.165 mg/ml ; 0.001 mol/l
Class : Soluble

Medicinal Chemistry

PAINS : 0.0 alert
Brenk : 1.0 alert
Leadlikeness : 1.0
Synthetic accessibility : 2.33

Safety of [ 14618-80-5 ]

Signal Word:Warning Class:N/A
Precautionary Statements:P261-P264-P271-P280-P302+P352-P304+P340+P312-P305+P351+P338-P332+P313-P337+P313-P403+P233-P405-P501 UN#:N/A
Hazard Statements:H315-H319-H335 Packing Group:N/A
GHS Pictogram:

Application In Synthesis of [ 14618-80-5 ]

* All experimental methods are cited from the reference, please refer to the original source for details. We do not guarantee the accuracy of the content in the reference.

  • Downstream synthetic route of [ 14618-80-5 ]

[ 14618-80-5 ] Synthesis Path-Downstream   1~5

  • 1
  • [ 926-39-6 ]
  • [ 14618-80-5 ]
  • [ 135065-70-2 ]
YieldReaction ConditionsOperation in experiment
49% With sodium hydroxide; In methanol; water; at 50℃; Example 1; (R)-Quinuclidin-3-yl 5-((S)-2-((4-amino-5-chloro-2-ethoxybenzamido)methyl)morpholino)pentanoate [Show Image] Mono-(2-amino-ethyl) sulfate (35.2 g, 250 mmol) was dissolved in 160 mL of aqueous sodium hydroxide solution (40percent) with stirring, and to the mixture was added with a solution of (R)benzyl glycidyl ether 1a (8.2 g, 50 mmol) in methanol. The reaction mixture was reacted overnight at 50°C and monitored by thin layer chromatography until the disappearance of the starting materials. The reaction mixture was diluted with 100 mL of water and 100 mL of concentrated hydrochloric acid, and extracted with dichloromethane (200 mL.x.3). The combined organic phase was washed successively with water (200 mL) and saturated brine (200 mL), dried over anhydrous magnesium sulfate, filtered and concentrated under reduced pressure. The residue was purified by silica gel column chromatography to obtain the title compound (R)-2-benzyloxymethyl-morpholine 1b (5.08 g, yield 49percent) as a yellow liquid. MS m/z (ESI): 208.7 [M+1]. 1H NMR (CDCl3, 400 MHz) delta 7.4-7.2 (m, 5H), 4.56 (s, 2H), 3.9 (d, 1H, J=11Hz) 3.8-3.35 (m, 4H), 2.92 (dd, 1H, J1=2.5Hz, J2=12.0Hz), 2.85-2.75 (m, 2H), 2.66 (dd, 1H, J1=10.5Hz, J2=12.0Hz), 2.4 (s, 1H).
49% With sodium hydroxide; In methanol; water; at 50℃; Mono-(2-amino-ethyl) sulfate (35.2 g, 250 mmol) was dissolved in 160 mL of aqueous sodium hydroxide solution (40percent) with stirring, and to the mixture was added with a solution of (R)benzyl glycidyl ether 1a (8.2 g, 50 mmol) in methanol. The reaction mixture was reacted overnight at 50° C. and monitored by thin layer chromatography until the disappearance of the starting materials. The reaction mixture was diluted with 100 mL of water and 100 mL of concentrated hydrochloric acid, and extracted with dichloromethane (200 mL.x.3). The combined organic phase was washed successively with water (200 mL) and saturated brine (200 mL), dried over anhydrous magnesium sulfate, filtered and concentrated under reduced pressure. The residue was purified by silica gel column chromatography to obtain the title compound (R)-2-benzyloxymethyl-morpholine 1b (5.08 g, yield 49percent) as a yellow liquid.MS m/z (ESI): 208.7 [M+1].1H NMR (CDCl3, 400 MHz) delta 7.4-7.2 (m, 5H), 4.56 (s, 2H), 3.9 (d, 1H, J=11 Hz), 3.8-3.35 (m, 4H), 2.92 (dd, 1H, J1=2.5 Hz, J2=12.0 Hz), 2.85-2.75 (m, 2H), 2.66 (dd, 1H, 1H, J1=10.5 Hz, J2=12.0 Hz), 2.4 (s, 1H).
With sodium hydroxide; In water; at 55℃; Step 1: (R)-2-(Benzyloxymethyl)morpholine: A stirred mixture of (R)-benzyl glycidyl ether (16.4 g) and 2-aminoethyl hydrogen sulfate (56.4 g) was treated with a solution of sodium hydroxide (16 g) in water (33 mL). The reaction mixture was warmed to 55 0C overnight. Water (250 mL) was added and the mixture extracted into toluene (200 mL x 3). The organic layers were combined, washed with brine and then dried over magnesium sulfate, filtered and concentrated to yield the subtitle compound as a pale oil (16.5 g) which was used directly in the next step.1H NMR delta(CDCl3):1.85-2.00 (IH, br s), 2.14-2.28 (IH, m), 2.38-2.50 (IH, m), 2.60- 2.95 (3H, m), 3.39-3.55 (2H, m), 3.57-3.70 (IH, m), 3.89 (IH, dm), 4.51-4.54 (2H, ABq), 7.18-7.36 (5H, m).
With water; sodium hydroxide; In methanol; at 40℃; for 2h; Step 1. (i?)-2-(Benzyloxymethyl)morpholine: To a stirred mixture of (R)-2- (benzyloxymethyl)oxirane (10.0 g, 60.9 mmol) and NaOH (19.49 g, 487.2 mmol) in H2O (46 mL) and MeOH (18 niL), there was added 2-aminoethyl hydrogen sulfate (36.8 g, 255.8 mmol) in portions. After addition was complete, the reaction mixture was stirred at 4O0C for 2 h. After cooling, the mixture was treated with NaOH (15.0 g, 375.0 mmol), followed by toluene (70 mL), and stirred at 650C overnight. The mixture was cooled, diluted with toluene (27 mL) and H2O (92 mL). The toluene layer was separated and the aqueous layer was extracted with CH2Cl2 (2 x 50 mL). The combined organic layers were concentrated to give crude (R)-2- (benzyloxymethyl)morpholine (~14 g), which was used without purification. MS m/z 208 (M+H+).
With sodium hydroxide; In methanol; water; toluene; at 40 - 65℃; To a stirred mixture of (2R)-2-[(benzy[oxy)methy[]oxirane (27.7 g, 0.17 mo[) and NaOH (54.0 g, 1.3 mo[) in water (130 mL) and MeOH (50 mL) was added 2-aminoethy[ hydrogen su[fate (100 g, 0.7 mo[) portionwise. After addition was comp[ete, the reaction mixture was stirred at 40 °C for 2 h. On coo[ing, the mixture was treated with a further portion of NaOH (40.5 g, 1 .0 mo[), fo[[owed by to[uene (200 mL) and stirred at 65 °C overnight. The mixture was coo[ed, di[uted with to[uene and water. The to[uene [ayer was separated and the aqueous [ayerextracted with DCM (2 x 100 mL). The combined organic [ayers were concentrated to give the tit[e compound, which was used in the next step without purification.
Benzyl-(R)-glycidyl ether (2.00 g, 12.2 mmol) and NaOH (4.00 g,100 mmol) in H2O (9.2 mL) and MeOH (3.6 mL) were treated with2-aminoethyl hydrogen sulphate (7.00 g, 49.59 mmol). The reactionmixturewas stirred for 90 min at 40 °C. The mixturewas allowed tocool to room temperature, toluene (14 mL) and NaOH (2.00 g,50.0 mmol) were added and then it was stirred overnight at 65 °C.Toluene (5 mL) and H2O (20 mL) were added and the organic layerwas separated. The water layer was extracted with CH2Cl2(2 10 mL). The combined organic layers were dried over Na2SO4,filtered and concentrated in vacuo to give crude amine which wastaken up in acetone (20 mL) and H2O (6 mL) at 0 °C. Di-tert-butyldicarbonate (2.60 g, 11.9 mmol) was added and the resultingmixture was stirred vigorously for 2 h. The acetone was removedunder reduced pressure and the aqueous solution was extractedwith CH2Cl2. The organic layer was washed with brine, dried overNa2SO4, filtered and concentrated in vacuo. FCC (hexane/EtOAc10:0 ? 7:3) afforded the title compound as a colorless oil in 43percent(over 2 steps). 1H NMR (300 MHz, 80 °C, DMSO-d6) delta ppm 1.41 (s,9 H) 2.69 (dd, J 12.9, 9.4 Hz, 1 H) 2.87 (ddd, J 13.2, 11.4, 3.5 Hz,1 H) 3.28e3.56 (m, 4 H) 3.68 (ddt, J 13.2, 3.0, 1.6 Hz, 1 H)3.75e3.86 (m, 2 H) 4.50 (s, 2 H) 7.22e7.38 (m, 5 H). 13C NMR(75 MHz, 80 °C, DMSO-d6) delta ppm 27.7, 43.0, 45.3, 65.1, 70.2, 72.2,73.6, 78.7, 126.9, 127.0, 127.7, 138.0, 153.6. HRMS (ESI-TOF) m/z:[M+H]+ Calcd for C17H26NO4 308.18563; Found 308.1867.
Step 1. (R)-2-(Benzyloxymethyl)morpholine. To a stirred mixture of (R)-2-(benzyloxymethyl)oxirane (10.0 g, 60.9 mmol) and NaOH (19.49 g, 487.2 mmol) in H2O (46 mL) and MeOH (18 mL), there was added 2-aininoethyl hydrogen sulfate (36.8 g, 255.8 mmol) in portions. After addition, the reaction mixture was- stirred at 4O0C for 2 h. After cooling, the mixture was treated with NaOH (15.0 g, 375.0 mmol) then toluene (70 mL) and stirred at 650C overnight. The mixture was cooled,. diluted with toluene (27 mL) and H2O (92 mL). The toluene layer was separated and the aqueous layer was extracted with CH2CI2 (2 x 50 mL). The combined organic layers were concentrated to give crude (R)-2-(benzyloxymethyl)morpholine (~14 g), which was used without purification. MS m/z 208 (M+H+).

  • 2
  • [ 15469-97-3 ]
  • [ 14618-80-5 ]
  • (2R)-1-(benzyloxy)-3-(1-trityl-1H-imidazol-2-yl)-2-propanol [ No CAS ]
YieldReaction ConditionsOperation in experiment
With n-butyllithium; In tetrahydrofuran; hexane; water; (i) (2R)-1-(benzyloxy)-3-(1-trityl-1H-imidazol-2-yl)-2-propanol In an argon atmosphere, n-butyllithium (1.6 M solution in hexane, 6.9 ml) was added drop by drop to a solution of 1-tritylimidazole (3.10 g) in THF (80 ml) under ice cooling. After stirring at the same temperature for 30 minutes, (R)-2-[(benzyloxy)methyl]oxirane (1.52 ml) was added. After stirring under ice cooling for 1.5 hours and at room temperature for 1 hour, water was added and the reaction mixture was extracted with ethyl acetate. The extract was washed with water and saline and dried over magnesium sulfate, after which it was concentrated under reduced pressure. The residue was purified by silica gel chromatography (eluent: ethyl acetate-hexane 1:1) to yield the titled compound (1.402 g) as a pale-yellow oily substance. 1H-NMR (CDCl3) delta: 2.06 (2H, dd, J=2.8 Hz, 18.0 Hz) 3.08 (1H, dd, J=5.4 Hz, 9.8 Hz), 3.21 (1H, dd, J=5.4 Hz, 9.8 Hz), 3.55-3.7 (1H, m), 4.36 (2H, s), 6.73 (1H, d, J=1.4 Hz), 6.93 (1H, d, J=1.4 Hz), 7.0-7.4 (20H, m).
With n-butyllithium; In tetrahydrofuran; hexane; water; (i) (2R)-1-(benzyloxy)-3-(1-trityl-1H-imidazol-2-yl)-2-propanol In an argon atmosphere, n-butyllithium (1.6 M solution in hexane, 6.9 ml) was added drop by drop to a solution of 1-tritylimidazole (3.10 g) in THF (80 mL) under ice cooling. After stirring at the same temperature for 30 minutes, (R)-2-[(benzyloxy)methyl]oxirane (1.52 mL) was added. After stirring under ice cooling for 1.5 hours and at room temperature for 1 hour, water was added and the reaction mixture was extracted with ethyl acetate. The extract was washed with water and saline and dried over magnesium sulfate, after which it was concentrated under reduced pressure. The residue was purified by silica gel chromatography (eluent: ethyl acetate-hexane 1:1) to yield the titled compound (1.402 g) as a pale-yellow oily substance. 1H-NMR (CDCl3) delta: 2.06 (2H, dd, J=2.8 Hz, 18.0 Hz), 3.08 (1H, dd, J=5.4 Hz, 9.8 Hz), 3.21 (1H, dd, J=5.4 Hz, 9.8 Hz), 3.55-3.7 (1H, m), 4.36 (2H, s), 6.73 (1H, d, J=1.4 Hz), 6.93 (1H, d, J=1.4 Hz), 7.0-7.4 (20H, m).
n-butyllithium (1.6M hexane solution, 6.9ml) was added dropwise to a solution of 1-tritylimidazole (3.10g) in THF (80mL) under ice-cooling in the argon atmosphere. After stirred at the same temperature for 30 minutes, (R)-2-[(benzyloxy)methyl]oxirane (1.52mL) was added. After stirred for 1.5 hours under ice-cooling and at room temperature for 1 hour, water was added to the reaction solution, followed by ethyl acetate. The extract was washed with water and a brine, dried with magnesium sulfate, and concentrated under reduced pressure. The residue was purified by subjecting to the silica column gel chromatography (eluent; ethyl acetate:hexane= 1:1) to obtain the title compound (1.402g) as a pale yellow oil. 1H-NMR (CDCl3) delta: 2.06 (2H, dd, J = 2.8Hz, 18.0Hz), 3.08 (1H, dd, J = 5.4Hz, 9.8Hz), 3.21 (1H, dd, J = 5.4Hz, 9.8Hz), 3.55-3.7 (1H, m), 4.36 (2H, s), 6.73 (1H, d, J = 1.4Hz), 6.93 (1H, d, J = 1.4Hz), 7.0-7.4 (20H, m).
To a THF solution (80 mL) of 1-tritylimidazol (3.10 g), n-butyllithium (1.6M hexane solution, 6.9 ml) was added dropwise in an argon atmosphere with ice-cooling. After stirring at the same temperature for 30 minutes, (R)-2-[(benzyloxy)methyl]oxirane (1.52 mL) was added thereto. After stirring for 1.5 hours with ice-cooling and stirring at room temperature for 1 hour, water was added to the reaction mixture and the mixture was extracted with ethyl acetate. The extract was washed with water and brine, dried over magnesium sulfate and then concentrated under reduced pressure. The residue was purified by subjecting to silica gel chromatography (eluent; ethyl acetate:hexane = 1:1) to obtain the title compound (1.402 g) as a pale yellow oily product. 1H-NMR (CDCl3) delta: 2.06 (2H, dd, J = 2.8Hz, 18.0Hz), 3.08 (1H, dd, J = 5.4Hz, 9.8Hz), 3.21 (1H, dd, J = 5.4Hz, 9.8Hz), 3.55-3.7 (1H, m), 4.36 (2H, s), 6.73 (1H, d, J = 1.4Hz), 6.93 (1H, d, J = 1.4Hz), 7.0-7.4 (20H, m).

  • 3
  • [ 926-39-6 ]
  • [ 14618-80-5 ]
  • C12H19NO6S [ No CAS ]
YieldReaction ConditionsOperation in experiment
With sodium hydroxide; In methanol; water; at 40℃; for 2h; To a stirred mixture of (7?)-2-(benzyloxymethyl)oxirane (10.0 g, 60.9 mmol) and NaOH (19.49 g, 487.2 mmol) in H2O (46 mL) and MeOH (18 mL), there was added 2-aminoethyl hydrogen sulfate (36.8 g, 255.8 mmol) in portions. After addition was complete, the reaction mixture was stirred at 4O0C for 2 h. After cooling, the mixture was treated with NaOH (15.0 g, 375.0 mmol), followed by toluene (70 mL), and stirred at 650C overnight. The mixture was cooled, diluted with toluene (27 mL) and H2O (92 mL). The toluene layer was separated and the aqueous layer was extracted with CH2Cl2 (2 x 50 mL). The combined organic layers were concentrated to give crude (i?)-2-(benzyloxymethyl)morpholine (~14 g), which was used without purification. MS m/z 208 (M+H+).
With sodium hydroxide; In methanol; water; at 40℃; for 2h; Step 1. (R)-2-(Benzyloxymethyl)morpholine <strong>[926-39-6]2-Aminoethyl hydrogen sulfate</strong> (36.8 g, 255.8 mmol) was added in portions to a stirred mixture of (R)-2-(benzyloxymethyl)oxirane (10.0 g, 60.9 mmol) and NaOH (19.49 g, 487.2 mmol) in H2O (46 mL) and MeOH (18 mL). After addition, the reaction mixture was stirred at 40° C. for 2 h. After cooling to rt, the mixture was treated with NaOH (15.0 g, 375.0 mmol), then toluene (70 mL) and stirred at 65° C. overnight. The mixture was cooled, diluted with toluene (27 mL) and H2O (92 mL). The toluene layer was separated and the aqueous layer was extracted with CH2Cl2 (2*50 mL). The combined organic layers were concentrated to give crude (R)-2-(benzyloxymethyl)morpholine (~14 g), which was used without purification. MS m/z 208 (M+H+).
With sodium hydroxide; In water; at 50℃; for 1h; 2g of S-(+)-2-(benzyloxymethyl)-oxirane and 7 g of 2-aminoethyl hydrogen sulfate were weighed into a 100 ml round bottle flask, 2 g of NaOH dissolved in H2O was added and the stirred mixture was heated at 50 0C for 1 hour. 4 g of NaOH dissolved in 10 ml H2O, solution was added to the stirred mixture, which was then heated at 55 0C for 16 h. After cooling the mixture to room temperature, it was diluted with 100 ml H2O and 100 ml dioxane and 2.66 g of di-tert-butyl dicarbonate was added. The mixture was stirred at room temperature for 5 hours, transferred into a separation funnel and extracted with 2 x 75 ml of toluene. Combined organic phases were washed with 2 x 50 ml of 1 M citric acid (aq.), once with brine, dried over Na2SO4 and concentrated in vacuo. The crude material was purified on silica yielding 2R-Benzyloxymethyl-morpholine-4-carboxylic acid tert-butyl ester 1.85 g (49percent) as a clear oil.
With sodium hydroxide; In water; at 40℃; for 2h; To a stirred mixture of (R)-2-(benzyloxymethyl)oxirane (10.0 g, 60.9 mmol) and NaOH (19.49 g, 487.2 mmol) in H2O (46 mL) and MeOH (18 mL), there was added 2-aminoethyl hydrogen sulfate (36.8 g, 255.8 mmol) in portions. After addition was complete, the reaction mixture was stirred at 40° C. for 2 h. After cooling, the mixture was treated with NaOH (15.0 g, 375.0 mmol), followed by toluene (70 mL), and stirred at 65° C. overnight. The mixture was cooled, diluted with toluene (27 mL) and H2O (92 mL). The toluene layer was separated and the aqueous layer was extracted with CH2Cl2 (2.x.50 mL). The combined organic layers were concentrated to give crude (R)-2-(benzyloxymethyl)morpholine (14 g), which was used without purification. MS m/z 208 (M+H+).
With sodium hydroxide; In methanol; water; at 40℃; for 2h; To a stirred mixture of (R)-2-(benzyloxymethyl)oxirane (10.0 g, 60.9 mmol) and NaOH (19.49 g, 487.2 mmol) in H2O (46 mL) and MeOH (18 mL), there was added 2-aminoethyl hydrogen sulfate (36.8 g, 255.8 mmol) in portions. After addition, the reaction mixture was stirred at 400C for 2 h. After cooling, the mixture was treated with NaOH (15.0 g, 375.0 mmol) then toluene (70 mL) and stirred at 650C overnight. The mixture was cooled, diluted with toluene (27 mL) and H2O (92 <n="183"/>mL). The toluene layer was separated and the aqueous layer was extracted with CH2Cl2 (2 x 50 mL). The combined organic layers were concentrated to give crude (R)-2-(benzyloxymethy])morpholine (-14 g), which was used without purification. MS m/z 208 (M+H+).

  • 4
  • [ 926-39-6 ]
  • [ 14618-80-5 ]
  • C12H19NO6S [ No CAS ]
YieldReaction ConditionsOperation in experiment
With sodium hydroxide; In water; at 50℃; for 1h; Step a) 2S-Benzyloxymethyl-morpholine-4-carboxylic acid tert-butyl ester3g of R-(+)-2-(benzyloxymethyl)-oxirane and 10.5 g of 2-aminomethyl hydrogen sulfate were weight in a 100 ml round bottle flask, 3 g of NaOH dissolved in H2O was added and the stirred mixture was heated at +50 0C for 1 hour. 6 g NaOH was dissolved in 10 ml H2O, solution was added to the stirred mixture, which was then heated at + 550C for 72 h. After cooling the mixture to room temperature, it was diluted with 100 ml H2O and 100 ml dioxane and 4.0 g of di-tert-butyl dicarbonate was added. The mixture was stirred at room temperature for 5 hours, transferred into a separation funnel and extracted with 2x75 ml of toluene. Combined organic phases were washed with 2 x 50 ml of 1 M citric acid (aq.), once with brine, dried over Na2SO4 and concentrated in vacuo. The crude material was purified on silica yielding 2S-Benzyloxymethyl-morpholine-4-carboxylic acid tert-butyl ester 2.55 g (45percent) as a clear oil.
  • 5
  • [ 926-39-6 ]
  • [ 14618-80-5 ]
  • C11H17NO5S [ No CAS ]
YieldReaction ConditionsOperation in experiment
With sodium hydroxide; In methanol; water; at 40℃; for 2h; To a stirred mixture of (R)-2-(benzyloxymethyl)oxirane (10.0 g, 60.9 mmol) and NaOH (19.49 g, 487.2 mmol) in H2O (46 mL) and MeOH (18 mL), there was added 2- aminoethyl hydrogen sulfate (36.8 g, 255.8 mmol) in portions. After addition the <n="177"/>reaction mixture was stirred at 4O°C for 2 h. After cooling, the mixture was treated with NaOH (15.0 g, 375.0 mmol) then toluene (70 mL) and stirred at 65°C overnight. The mixture was cooled, diluted with toluene (27 mL) and H2O (92 mL). The toluene layer was separated and the aqueous layer was extracted with CH2Cl2 (2 x 50 mL). The combined organic layers were concentrated to give crude (R)-2-(benzyloxymethyl)morpholine (~14 g), which was used without purification. MS m/z 208 (M+H+).
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