[ CAS No. 614730-97-1 ] {[proInfo.proName]}

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2D 3D

Structure of 614730-97-1 * Storage: {[proInfo.prStorage]}

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Quality Control of [ 614730-97-1 ]

COA NMR CNMR HPLC LC-MS

Related Doc. of [ 614730-97-1 ]

SDS Specification

Alternatived Products of [ 614730-97-1 ]

Product Details of [ 614730-97-1 ]

CAS No. :	614730-97-1	MDL No. :	MFCD08062513
Formula :	C₁₁H₂₀FNO₃	Boiling Point :	No data available
Linear Structure Formula :	-	InChI Key :	BWZOULIMVKCGII-UHFFFAOYSA-N
M.W :	233.28	Pubchem ID :	22248400
Synonyms :

Calculated chemistry of [ 614730-97-1 ] Expand+

Physicochemical Properties

Num. heavy atoms :	16
Num. arom. heavy atoms :	0
Fraction Csp3 :	0.91
Num. rotatable bonds :	4
Num. H-bond acceptors :	4.0
Num. H-bond donors :	1.0
Molar Refractivity :	62.65
TPSA :	49.77 ?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) :	-6.91 cm/s

Lipophilicity

Log Po/w (iLOGP) :	2.56
Log Po/w (XLOGP3) :	1.14
Log Po/w (WLOGP) :	1.76
Log Po/w (MLOGP) :	1.3
Log Po/w (SILICOS-IT) :	1.35
Consensus Log Po/w :	1.62

Druglikeness

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

Water Solubility

Log S (ESOL) :	-1.74
Solubility :	4.24 mg/ml ; 0.0182 mol/l
Class :	Very soluble
Log S (Ali) :	-1.78
Solubility :	3.88 mg/ml ; 0.0166 mol/l
Class :	Very soluble
Log S (SILICOS-IT) :	-1.61
Solubility :	5.74 mg/ml ; 0.0246 mol/l
Class :	Soluble

Medicinal Chemistry

PAINS :	0.0 alert
Brenk :	0.0 alert
Leadlikeness :	1.0
Synthetic accessibility :	2.27

Safety of [ 614730-97-1 ]

Signal Word:	Warning	Class:
Precautionary Statements:	P261-P280-P305+P351+P338	UN#:
Hazard Statements:	H302-H315-H319-H332-H335	Packing Group:
GHS Pictogram:

Application In Synthesis of [ 614730-97-1 ]

* 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 [ 614730-97-1 ]

[ 614730-97-1 ] Synthesis Path-Downstream 1~3

1
[ 614730-97-1 ]
[ 620611-27-0 ]

Reference： [1]Patent: US2011/256064,2011,A1
[2]Patent: EP2377860,2011,A1

2
[ 614730-97-1 ]
[ 1354961-13-9 ]
tert-butyl 4-((4-(tert-butoxycarbonyl)-2-chloro-5-fluorophenoxy)methyl)-4-fluoropiperidine-1-carboxylate [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
73%	With caesium carbonate; In dimethyl sulfoxide; at 80℃; for 4h;	To a mixture of tert-butyl 4-fluoro-4- (hydroxymethyl) piperidine-1-carboxylate (4.60 g, 19.70 mmol) and tert-butyl 5-chloro-2, 4-difluorobenzoate (4.89 g, 19.70 mmol) in dimethyl sulfoxide (50 mL) was added cesium carbonate (9.65 g, 29.60 mmol) and the reaction mixture was heated at 80 for 4 hours. After cooling to an ambient temperature, water (50 mL) was added, and then extracted with ethyl acetate (3 x 100 mL) . The organic layer was washed with brine (2×50 mL) , dried over anhydrous sodium sulfate and filtered. The filtrate was concentrated in vacuo and the residue was purified by silica gel column chromatography eluting with gradient of 0-30 ethyl acetate in hexanes to afford the title compound as a colorless gum (6.60 g, 73) :1H NMR (300 MHz, CDCl3) δ 7.82 (d, J7.6 Hz, 1H) , 6.58 (d, J11.8 Hz, 1H) , 3.90-4.10 (m, 3H) , 3.07 (t, J12.4 Hz, 2H) , 1.98-1.89 (m, 3H), 1.84-1.56 (m, 2H) , 1.51 (s, (H) , 1.40 (s, 9H) MS (ES+) m/z 464.1, 462.1 (M+1) .
73%	With caesium carbonate; In dimethyl sulfoxide; at 80℃; for 4h;Inert atmosphere;	Step 1 Preparation of tert-butyl 4-((4-(tert-butoxycarbonyl)-2-chloro-5-fluorophenoxy)methyl)-4-fluoropiperidine-1-carboxylate (0419) tert-butyl 4-fluoro-4-(hydroxymethyl)piperidine-1-carboxylate (3.20 g, 13.7 mmol) and <strong>[1354961-13-9]tert-butyl 5-chloro-2,4-difluorobenzoate</strong> (3.40 g, 13.7 mmol) in dimethyl sulfoxide (50 mL) was added cesium carbonate (8.94 g, 27.5 mmol) and the reaction mixture was heated at 80 C. for 4 h. After cooling to an ambient temperature, added water (50 mL) and extracted with ethyl acetate (3×100 mL). The organic layer was washed brine (2×50 mL), dried over anhydrous sodium sulfate and filtered. The solvent was concentrated in vacuo and the residue was purified by silica gel column chromatography using gradient of 0-30% ethyl acetate in hexanes as eluent to afford the title compound as a colorless gum (6.6 g, 73% yield): 1H NMR (300 MHz, CDCl3) δ 7.82 (d, J=7.6 Hz, 1H), 6.58 (d, J=11.8 Hz, 1H), 3.90-4.10 (m, 3H), 3.07 (t, J=12.4 Hz, 2H), 1.98-1.89 (m, 3H), 1.84-1.56 (m, 2H), 1.51 (s, (H), 1.40 (s, 9H); MS (ES+) m/z 464.1, 462.1 (M+1).

Reference： [1]Patent: WO2015/78374,2015,A1 .Location in patent: Page/Page column 415
[2]Patent: US2016/340309,2016,A1 .Location in patent: Paragraph 0419; 0420

3
[ 614731-04-3 ]
[ 614730-97-1 ]

Yield	Reaction Conditions	Operation in experiment
100%	With borane-THF; In tetrahydrofuran; at 0 - 20℃; for 5h;	1-(tert-Butoxycarbonyl)-4-fluoropiperidine-4-carboxylic acid 13a (5.0 g, 20 mmol) was dissolved in 50 mL of THF.A borane tetrahydrofuran solution (50 mL, 1 M/THF) was added dropwise at 0 C, and the mixture was reacted at room temperature for 5 hours. Slow down in the reaction solution at 0 CThe reaction was quenched by slowly adding 20 mL of methanol. Concentrate under reduced pressure to remove the solvent. Add 50 mL of water and extract with ethyl acetate (50 mL×3).The combined organic layers were washed with EtOAc EtOAc (EtOAc)Fluor-4-(hydroxymethyl)piperidine-1-carboxylic acid tert-butyl ester 13b (4.7 g, colorless oil), yield: 100%.
98%	With borane-THF; In tetrahydrofuran; for 32h;Reflux;	To a solution of 1- (tert-butoxycarbonyl) -4-fluoropiperidine-4-carboxylic acid (5.00 g, 20.20 mmol) in tetrahydrofuran (100 mL) was added a solution of borane tetrahydrofuran complex (30.3 mL, 30.30 mmol, 1.0 M solution in tetrahydrofuran) . The reaction mixture was refluxed for 16 hours, and then another 24 mL of borane tetrahydrofuran complex was added and continued to reflux for another 16 hours. After cooling to ambient temperature the reaction mixture poured onto ice-cold water (50 mL) and saturated ammonium chloride (100 mL) , and extracted with ethyl acetate (3 x 100 mL) , dried over anhydrous sodium sulfate and filtered. The filtrate was concentrated to afford the title compound (4.60 g, 98) . Which was used in the next step without further purification: MS (ES+) m/z 234.1 (M +1) .
	With borane-THF; In tetrahydrofuran; for 32h;Reflux; Inert atmosphere;	Step 1. Preparation of tert-Butyl 4-fluoro-4-(hydroxymethyl)piperidine-1-carboxylate (0341) <strong>[614731-04-3]1-(tert-butoxycarbonyl)-4-fluoropiperidine-4-carboxylic acid</strong> (5.00 g, 20.20 mmol) in tetrahydrofuran (100 mL) was added a solution of borane tetrahydrofuran complex (30.3 mL, 30.30 mmol, 1.0 M solution in tetrahydrofuran). The reaction mixture was refluxed for 16 hours, and then another 24 mL of borane tetrahydrofuran complex was added and continued to reflux for another 16 hours. After cooling to ambient temperature the reaction mixture poured onto ice-cold water (50 mL) and saturated ammonium chloride (100 mL), and extracted with ethyl acetate (3×100 mL), dried over anhydrous sodium sulfate and filtered. The filtrate was concentrated to afford the title compound (4.60 g, 98%). Which was used in the next step without further purification: MS (ES+) m/z 234.1 [M+H]+.

Reference： [1]Patent: CN109574927,2019,A .Location in patent: Paragraph 0465; 0467-0470
[2]Patent: WO2015/78374,2015,A1 .Location in patent: Page/Page column 415
[3]Patent: US2016/340309,2016,A1 .Location in patent: Paragraph 0341; 0342

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Technical Information

? Acyl Group Substitution ? Alkyl Halide Occurrence ? Appel Reaction ? Bouveault-Blanc Reduction ? Buchwald-Hartwig C-N Bond and C-O Bond Formation Reactions ? Catalytic Hydrogenation ? Chan-Lam Coupling Reaction ? Chugaev Reaction ? Complex Metal Hydride Reductions ? Corey-Kim Oxidation ? Dess-Martin Oxidation ? Ester Cleavage ? Hydride Reductions ? Jones Oxidation ? Lawesson's Reagent ? Martin's Sulfurane Dehydrating Reagent ? Mitsunobu Reaction ? Moffatt Oxidation ? Oxidation of Alcohols by DMSO ? Preparation of Alcohols ? Preparation of Amines ? Reactions of Alcohols ? Reactions of Amines ? Reactions with Organometallic Reagents ? Ritter Reaction ? Sharpless Olefin Synthesis ? Specialized Acylation Reagents-Carbodiimides and Related Reagents ? Specialized Acylation Reagents-Ketenes ? Swern Oxidation

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Code	Phrase
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P220	Keep/Store away from clothing/combustible materials.
P221	Take any precaution to avoid mixing with combustibles
P222	Do not allow contact with air.
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P230	Keep wetted
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P233	Keep container tightly closed.
P234	Keep only in original container.
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P302 + P334	IF ON SKIN: Immerse in cool water/wrap in wet bandages.
P302 + P350	IF ON SKIN: Gently wash with plenty of soap and water.
P303 + P361 + P353	IF ON SKIN (or hair): Remove/Take off Immediately all contaminated clothing. Rinse SKIN with water/shower.
P304 + P312	IF INHALED: Call a POISON CENTER or doctor/physician if you feel unwell.
P304 + P340	IF INHALED: Remove victim to fresh air and Keep at rest in a position comfortable for breathing.
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P337 + P313	IF eye irritation persists: Get medical advice/attention.
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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. 614730-97-1 ] {[proInfo.proName]}

Quality Control of [ 614730-97-1 ]

Related Doc. of [ 614730-97-1 ]

Product Details of [ 614730-97-1 ]

Calculated chemistry of [ 614730-97-1 ] Expand+

Physicochemical Properties

Pharmacokinetics

Lipophilicity

Druglikeness

Water Solubility

Medicinal Chemistry

Safety of [ 614730-97-1 ]

Application In Synthesis of [ 614730-97-1 ]

[ 614730-97-1 ] Synthesis Path-Downstream 1~3

Technical Information

Related Functional Groups of [ 614730-97-1 ]

Fluorinated Building Blocks

Alcohols

Amides

Related Parent Nucleus of [ 614730-97-1 ]

Aliphatic Heterocycles

Piperidines

Precautionary Statements-General

Prevention

Response

Storage

Disposal

Physical hazards

Health hazards

Environmental hazards

Inquiry

Related Functional Groups of
[ 614730-97-1 ]

Related Parent Nucleus of
[ 614730-97-1 ]