[ CAS No. 20989-17-7 ] {[proInfo.proName]}

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Quality Control of [ 20989-17-7 ]

COA NMR CNMR HPLC LC-MS

Related Doc. of [ 20989-17-7 ]

SDS Specification

Alternatived Products of [ 20989-17-7 ]

Product Details of [ 20989-17-7 ]

CAS No. :	20989-17-7	MDL No. :	MFCD00064404
Formula :	C₈H₁₁NO	Boiling Point :	-
Linear Structure Formula :	H₂NCH(C₆H₅)CH₂OH	InChI Key :	IJXJGQCXFSSHNL-MRVPVSSYSA-N
M.W :	137.18	Pubchem ID :	134797
Synonyms :	(+)-Phenylglycinol	Chemical Name :	(S)-2-Amino-2-phenylethanol

Calculated chemistry of [ 20989-17-7 ] Expand+

Physicochemical Properties

Num. heavy atoms :	10
Num. arom. heavy atoms :	6
Fraction Csp3 :	0.25
Num. rotatable bonds :	2
Num. H-bond acceptors :	2.0
Num. H-bond donors :	2.0
Molar Refractivity :	40.08
TPSA :	46.25 ?2

Pharmacokinetics

GI absorption :	High
BBB permeant :	No
P-gp substrate :	No
CYP1A2 inhibitor :	No
CYP2C19 inhibitor :	No
CYP2C9 inhibitor :	No
CYP2D6 inhibitor :	No
CYP3A4 inhibitor :	No
Log Kp (skin permeation) :	-7.04 cm/s

Lipophilicity

Log Po/w (iLOGP) :	1.3
Log Po/w (XLOGP3) :	0.13
Log Po/w (WLOGP) :	0.35
Log Po/w (MLOGP) :	0.94
Log Po/w (SILICOS-IT) :	0.98
Consensus Log Po/w :	0.74

Druglikeness

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

Water Solubility

Log S (ESOL) :	-1.08
Solubility :	11.3 mg/ml ; 0.0823 mol/l
Class :	Very soluble
Log S (Ali) :	-0.66
Solubility :	30.2 mg/ml ; 0.22 mol/l
Class :	Very soluble
Log S (SILICOS-IT) :	-1.89
Solubility :	1.78 mg/ml ; 0.013 mol/l
Class :	Soluble

Medicinal Chemistry

PAINS :	0.0 alert
Brenk :	0.0 alert
Leadlikeness :	1.0
Synthetic accessibility :	1.19

Safety of [ 20989-17-7 ]

Signal Word:	Warning	Class:	N/A
Precautionary Statements:	P261-P305+P351+P338	UN#:	N/A
Hazard Statements:	H315-H319-H335	Packing Group:	N/A
GHS Pictogram:

Application In Synthesis of [ 20989-17-7 ]

* 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.

Upstream synthesis route of [ 20989-17-7 ]
Downstream synthetic route of [ 20989-17-7 ]

[ 20989-17-7 ] Synthesis Path-Upstream 1~1

1
[ 20989-17-7 ]
[ 1260672-03-4 ]

Reference： [1] Patent: WO2016/168641, 2016, A1,

[ 20989-17-7 ] Synthesis Path-Downstream 1~10

1
[ 34374-88-4 ]
[ 20989-17-7 ]
C₃₃H₃₃N₃O₆ [ No CAS ]

Reference： [1]Tetrahedron Asymmetry,2007,vol. 18,p. 2820 - 2827

2
[ 22280-60-0 ]
[ 20989-17-7 ]
(S)-2-(6-methyl-5-nitro-pyridin-2-ylamino)-2-phenyl-ethanol [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
63%	With triethylamine; In dimethyl sulfoxide; at 140℃; for 0.333333h;Microwave irradiation;	Example 10 (S)-2-(6-Methyl-5-nitro-pyridin-2-ylamino)-2-phenyl-ethanol 6-Chloro-3-nitro-2-picoline (22 mg, 0.13 mmol) was coupled with (2-amino-2-phenyl)- propanol (34 mg, 0.25 mmol) in triethylamine (0.030 mL, 0.25 mmol) in DMSO (1 mL). The reaction was heated to 140 °C for 1200 seconds in a microwave oven (Parameters : high absorbance, fixed holding time, pre-stirring 25 seconds). The mixture was diluted with 20 mL of EtOAc and then washed with NI-14CI (aq) three times. The organic phase was collected, dried with anhydrous MgSO4 and filtered. The dry organic phase was evaporated and purification on silica column with 5: 1 n-Heptane : EtOAc gave 22 mg (63percent) of (R)-2- (6-methyl-5-nitro-pyridin-2-ylamino) 2-phenyl-ethanol as a yellow solid.

Reference： [1]Patent: WO2005/42464,2005,A1 .Location in patent: Page/Page column 34-35

3
[ 20989-17-7 ]
[ 4385-76-6 ]
[ 1127307-61-2 ]

Yield	Reaction Conditions	Operation in experiment
56%	With 4-methyl-morpholine; benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; In tetrahydrofuran; for 24h;	4-Pyridin-4-ylbenzoic acid (5.86 g, 29.4 mmol) was dissolved in 300 ml of THF. Subsequently, N-methylmorpholine (4.04 g, 29.5 mmol), (2S)-2-amino-2-phenylethanol (3.96 g, 29.3 mmol) and 1-hydroxybenzotriazol (3.96 g, 29.3 mmol) were added. Finally EDC (5.63 g, 29.4 mmol) was added over a period of 5 min and the heterogenic reaction mixture was stirred for 24 h, whereupon an oily precipitation occured. After evaporation of the solvent under reduced pressure the residue was dissolved in DCM (500 ml), washed twice with aqueous NaOH (50 ml of a 2 M solution) and subsequently with water. After drying the organic phase over sodium sulfate and evaporating the solvent under reduced pressure the raw title compound was obtained as an oily residue (8.4 g). Column chromatography (silica gel; eluent: EtOAc with an increasing amount of MeOH (0 up to 5percent)) yielded the pure title compound (5.2 g, yield: 56percent) as a white crystalline product.1H NMR (400 MHz, DMSO-d6): 8,83 (d, 1 H), 8,67 (d, 2H), 8,06 (d, 2H), 7,93 (d, 2H), 7,77 (d, 2H), 7,41 (d, 2H), 7,32 (dd, 2H), 7,23 (dd, 1 H), 5,14-5,07 (m, 1 H), 4,98 (t, 1 H), 3,79-3,63 (m, 2H). Formula: C20 Hi8 N2 O2 CaIc MW: 318,37 MS: m/z: 319.1 (M+H).

Reference： [1]Patent: WO2009/27392,2009,A1 .Location in patent: Page/Page column 183

4
[ 20989-17-7 ]
[ 149437-76-3 ]
[ 1187468-19-4 ]

Yield	Reaction Conditions	Operation in experiment
	In toluene; at 140℃; for 20h;Molecular sieve;	Synthesis 67; (S)-2-[(/?)-2-(4-Fluoro-phenyl)-piperidin-1-yl]-2-phenyl-ethanol hydrochloride <n="140"/>; 5-(4-Fluoro-phenyl)-5-oxo-pentanoic acid (1g, 5.10 mmol) and (S)-(+)-2-phenylglycinol (0.839 g, 6.12 mmol) in toluene (15 ml.) together with 4A molecular sieves was heated at 1400C under Dean-Stark conditions for 20 hours. The reaction mixture was filtered through Celite, evaporated and the residue dissolved in ethyl acetate then re- evaporated. The crude material was purified by column chromatography eluting with 20- 40% ethyl acetate in cyclohexane to afford (3S,8aS)-8a-(4-fluoro-phenyl)-3-phenyl- hexahydro-oxazolo[3,2-a]pyridin-5-one (1.08g).

Reference： [1]Patent: WO2009/112845,2009,A1 .Location in patent: Page/Page column 138-139

5
[ 54221-96-4 ]
[ 20989-17-7 ]
[ 1227845-05-7 ]

Yield	Reaction Conditions	Operation in experiment
	In tetrahydrofuran; for 4h;Inert atmosphere; Reflux;	Preparation of Example 72 - (3.pound.4fl)-iV-((y)-l-(6-methoxypyridin-2- yl)ethyl)-4-(4-(trifluoromethyl)phenyl)pyrrolidine-3-carboxamide; (S)-I -(6-methoxypyridin-2-yl)ethanamine (51) was prepared by the following procedures.[0216] In a 250 mL of round bottom flask, equipped with Dean-Stark trap and a reflux condenser, 6-methoxypicolinaldehyde 45 (500 mg, 3.65 mmol), (S)-2 (+)- phenylglycinol 46 (500 mg, 3.65 mmol) and anhydrous THF (30 mL) were mixed and heated at reflux under argon for 4 h. (S,E)-2-((6-methoxypyridin-2-yl)methyleneamino)- 2-phenylethanol 47 was used directly in the next step without further purification.[0217] HDMS (470 mg, 2.92 mmol), (NH4)2SO4 (53 mg, 0.4 mmol) and anhydrous THF (15 mL) were added to compound 47 (934 mg, 3.65 mmol). The reaction mixture was heated at 800C for 2 h under argon. Then the solvent was removed in vacuo to afford crude (S,E)-N-((6-methoxypyridin-2-yl)methylene)-l-phenyl-2-(trimethylsilyloxy)ethanamine 48 (1.2 g).[0218] In a 100 mL of round bottom flask (flame-dried), at -78 "C, were added anhydrous THF (10 mL) and CH3MgBr (3.0 M in Et2O, 3.5 mL). At -50 0C, compound 48 (1.2 g, 3.65 mmL) in anhydrous THF (10 mL) was added dropwise. The reaction mixture was stirred at -40 0C for 1 h, and at rt. for 1 h. The reaction was then quenched with a cold, sat. NH4Cl with stirring at 00C. EtOAc was added and layers were separated. The organic layer was concentrated to afford (S)-N-((S)-l-(6-methoxypyridin- 2-yl)ethyl)-l-phenyl-2-(trimethylsilyloxy)ethanamine 49 (1 g).[0219] A solution of compound 49 (1 g, 0.29 mmol) in THF was cooled to 0 °C, H2SO4 (2.5 M, 5 rnL) was added dropwise with stirring. The resulting mixture was stirred at rt. for 2 h. The mixture was basified with 2N NaOH at 0 °C and extracted with EtOAc (3 x 30 mL). Combined organic layers were dried over Na2SO4 and concentrated. The residue was purified with flash column (eluted with 30percent EtOAc/hexane) to give (S)- 2-((S)-l-(6-methoxypyridin-2-yl)ethylamino)-2-phenylethanol 50 (860 mg).[0220] Methylamine in water (40 percent in water, 10 mL) was added to a solution of compound 50 (860 m g, 3.16 mmol) in MeOH (15 mL). At 0 0C, H5IO6 (4.33 g,) in water (15 mL) was added dropwise. White precipitates were formed. The resulting mixture was stirred at rt overnight. EtOAc and water were added. Organic layer was separated, and aq. layer was extracted with EtOAc. Combined organic layers were concentrated. The crude product was purified by prep. HPLC to give (S)-I -(6- methoxypyridin-2-yl)ethanamine 51 (80 mg).[0221] Data for compound 51: 1H NMR (400 MHz, CD3OD) delta 7.62 (t, IH), 6.89 (d, IH), 6.64 (d, IH), 3.97 (m, IH), 3.90 (s, 3H), 1.42 (d, 3H). The above method can be used to prepare other chiral amines. For examples, the chiral amines used in Example 117, 118 and 120. Example 72[0223] Example 72 was prepared from (-)-5 (prepared from Procedure K) and (S)-l-(6-methoxypyridin-2-yl)ethanamine 51 using the similar procedures in Example 96. 1H NMR Data for Example 72 (see Table 5). Preparation of Example 91 - (3S,4R)-4-(3,4-dichlorophenyl)-N-((S)-l-(3- methoxyphenyl)ethyl)pyrrolidine-3-carboxamide

Reference： [1]Patent: WO2010/59922,2010,A1 .Location in patent: Page/Page column 46-47

6
[ 6223-83-2 ]
[ 20989-17-7 ]
[ 1424273-26-6 ]
[ 1424273-27-7 ]

Yield	Reaction Conditions	Operation in experiment
53%; 24%	With carbon tetrabromide; triethylamine; triphenylphosphine; In toluene; at 90℃; for 14.0h;Inert atmosphere;	General procedure: A 200 mL three-necked flask equipped with a condenser was charged with Ph3P (2.20 g, 8.4 mmol), Et3N (0.85 g, 8.4 mmol), CBr4 (16.8 g, 8.4 mmol), substrate 1 (3.3 mmol), and aromatic acid 2 (2.8 mmol) in toluene (15.0 mL) under a nitrogen atmosphere. The solution was stirred for approximately 20 min at room temperature, then the mixture was heated at 90 C with stirring for 6-14 h. The solvent was evaporated under reduced pressure, and the residue was diluted with petroleum ether (60-90 C) and filtered. The residual solid Ph3PO and Et3N·HBr was washed with petroleum ether three times. The filtrate was concentrated, and the residue was separated by column chromatography (ethyl acetate/petroleum ether, 1:8) to afford product 3 and 3?. If the mixture was processed after stirring for 0.5 h at 90 C, intermediate 6 was obtained by column chromatography (ethyl acetate/petroleum ether=1:8).

Reference： [1]Tetrahedron,2013,vol. 69,p. 2150 - 2156

7
[ 20989-17-7 ]
[ 56844-12-3 ]
[ 1432742-18-1 ]

Yield	Reaction Conditions	Operation in experiment
93%	With triethylamine; In N,N-dimethyl-formamide; at 20℃;	At room temperature, the compound 4-chloro-6-bromo-thieno [2,3-d] pyrimidine (1g, 4.0mmol) and L- glycine benzyl alcohol (1g, 7.2mmol) Was dissolved in N, N- dimethylformamide (20ml, 0.259mol) was added dropwise 1ml triethylamine (363mg, 7.19mmol), Stirred at room temperature until the reaction was complete as monitored by TLC starting material, was added 200ml of water, vacuum filtration, the cake was washed with water (100ml * 2) : The compound 2- (6-bromo - thieno [2,3-d] pyrimidin-4-yl-amine) -2-phenyl-1- ethanol (1.3 g of, as a pale yellow solid), yield: 93%
86%	In butan-1-ol; at 145℃; for 24h;	General procedure: Compound 1 (1.00 g, 4.01 mmol) was mixed with the benzylamine (12.03 mmol) and 1-butanol (3.5 mL) and agitated at 145 C for 18-24 h. Then the mixture was cooled to rt, diluted with water (50 mL) and diethyl ether (150 mL) or EtOAc (150 mL). After phase separation, the water phase was extracted with more diethyl ether (2 × 50 mL) or EtOAc (2 × 50 mL). The combined organic phases were washed with saturated aq NaCl solution (50 mL), dried over anhydrous Na2SO4, filtered and concentrated in vacuo, before the crude oil was dried under reduced pressure to constant weight to remove excess benzylamine. The compounds were purified by silica-gel column chromatography or crystallized as specified for each individual compound

Reference： [1]Patent: CN103087077,2016,B .Location in patent: Paragraph 0054; 0057; 0059
[2]European Journal of Medicinal Chemistry,2014,vol. 75,p. 354 - 374

8
[ 876343-10-1 ]
[ 20989-17-7 ]
[ 1643962-38-2 ]

Yield	Reaction Conditions	Operation in experiment
	In butan-1-ol; at 145℃;	General procedure: Compound 1a-d or 54 (1 mmol) was mixed with the selected amine, 2-25, (3 mmol) and n-butanol (5 ml) and agitated at145 C for 14-24 h. Then the mixture was cooled to 22 C, dilutedwith water (15 ml) and ethyl acetate (40 ml). After phase separation,the water phase was back extracted with more ethyl acetate(2 10 ml). The combined organic phases were washed with brine(10 ml), dried over anhydrous Na2SO4, filtered and concentrated invacuo, before the crude mixture was purified as specified for eachindividual compound

Reference： [1]European Journal of Pharmaceutical Sciences,2014,vol. 59,p. 69 - 82

9
[ 57772-50-6 ]
[ 20989-17-7 ]
9-methyl-3-phenyl-2,3,4,5-tetrahydro-1H-1,4-benzodiazepine [ No CAS ]

Reference： [1]European Journal of Organic Chemistry,2015,vol. 2015,p. 1068 - 1074

10
[ 6624-49-3 ]
[ 20989-17-7 ]
C₁₈H₁₆N₂O₂ [ No CAS ]

Reference： [1]Chemical Communications,2019,vol. 55,p. 5902 - 5905

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Isomers

Technical Information

? Appel Reaction ? Benzylic Oxidation ? Birch Reduction ? Blanc Chloromethylation ? Buchwald-Hartwig C-N Bond and C-O Bond Formation Reactions ? Chan-Lam Coupling Reaction ? Chugaev Reaction ? Corey-Kim Oxidation ? Dess-Martin Oxidation ? Friedel-Crafts Reaction ? Hydride Reductions ? Hydrogenolysis of Benzyl Ether ? Jones Oxidation ? Leuckart-Wallach Reaction ? Mannich Reaction ? Martin's Sulfurane Dehydrating Reagent ? Mitsunobu Reaction ? Moffatt Oxidation ? Oxidation of Alcohols by DMSO ? Petasis Reaction ? Preparation of Alcohols ? Preparation of Alkylbenzene ? Preparation of Amines ? Reactions of Alcohols ? Reactions of Amines ? Reactions of Benzene and Substituted Benzenes ? Reactions with Organometallic Reagents ? Ritter Reaction ? Sharpless Olefin Synthesis ? Specialized Acylation Reagents-Vilsmeier Reagent ? Swern Oxidation ? Ugi Reaction ? Vilsmeier-Haack Reaction

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Similar Product of
[ 20989-17-7 ]

A812348[ 88026-82-8 ]

(S)-2-Amino-2-phenylethan-1-ol hydrochloride

Reason: Free-salt

Ghs Precautionary Statements

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P306 + P360	IF ON CLOTHING: Rinse Immediately contaminated CLOTHING and SKIN with plenty of water before removing clothes.
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Physical hazards
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H261	In contact with water releases flammable gas
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H271	May cause fire or explosion; strong oxidizer
H272	May intensify fire; oxidizer
H280	Contains gas under pressure; may explode if heated
H281	Contains refrigerated gas; may cause cryogenic burns or injury
H290	May be corrosive to metals
Health hazards
Code	Phrase
H300	Fatal if swallowed
H301	Toxic if swallowed
H302	Harmful if swallowed
H303	May be harmful if swallowed
H304	May be fatal if swallowed and enters airways
H305	May be harmful if swallowed and enters airways
H310	Fatal in contact with skin
H311	Toxic in contact with skin
H312	Harmful in contact with skin
H313	May be harmful in contact with skin
H314	Causes severe skin burns and eye damage
H315	Causes skin irritation
H316	Causes mild skin irritation
H317	May cause an allergic skin reaction
H318	Causes serious eye damage
H319	Causes serious eye irritation
H320	Causes eye irritation
H330	Fatal if inhaled
H331	Toxic if inhaled
H332	Harmful if inhaled
H333	May be harmful if inhaled
H334	May cause allergy or asthma symptoms or breathing difficulties if inhaled
H335	May cause respiratory irritation
H336	May cause drowsiness or dizziness
H340	May cause genetic defects
H341	Suspected of causing genetic defects
H350	May cause cancer
H351	Suspected of causing cancer
H360	May damage fertility or the unborn child
H361	Suspected of damaging fertility or the unborn child
H361d	Suspected of damaging the unborn child
H362	May cause harm to breast-fed children
H370	Causes damage to organs
H371	May cause damage to organs
H372	Causes damage to organs through prolonged or repeated exposure
H373	May cause damage to organs through prolonged or repeated exposure
Environmental hazards
Code	Phrase
H400	Very toxic to aquatic life
H401	Toxic to aquatic life
H402	Harmful to aquatic life
H410	Very toxic to aquatic life with long-lasting effects
H411	Toxic to aquatic life with long-lasting effects
H412	Harmful to aquatic life with long-lasting effects
H413	May cause long-lasting harmful effects to aquatic life
H420	Harms public health and the environment by destroying ozone in the upper atmosphere

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[ CAS No. 20989-17-7 ] {[proInfo.proName]}

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