[ CAS No. 942190-60-5 ] {[proInfo.proName]}

Name: 942190-60-5|tert-Butyl 3-cyano-3-((trimethylsilyl)oxy)pyrrolidine-1-carboxylate|95%
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SKU: A264015
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Quality Control of [ 942190-60-5 ]

COA NMR CNMR HPLC LC-MS

Related Doc. of [ 942190-60-5 ]

SDS Specification

Alternatived Products of [ 942190-60-5 ]

Product Details of [ 942190-60-5 ]

CAS No. :	942190-60-5	MDL No. :	MFCD24466109
Formula :	C₁₃H₂₄N₂O₃Si	Boiling Point :	-
Linear Structure Formula :	-	InChI Key :	PVWFGQURJWJHJF-UHFFFAOYSA-N
M.W :	284.43	Pubchem ID :	68215451
Synonyms :

Calculated chemistry of [ 942190-60-5 ]

Physicochemical Properties

Num. heavy atoms :	19
Num. arom. heavy atoms :	0
Fraction Csp3 :	0.85
Num. rotatable bonds :	5
Num. H-bond acceptors :	4.0
Num. H-bond donors :	0.0
Molar Refractivity :	79.75
TPSA :	62.56 Å²

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) :	-6.5 cm/s

Lipophilicity

Log Po/w (iLOGP) :	3.47
Log Po/w (XLOGP3) :	2.16
Log Po/w (WLOGP) :	2.36
Log Po/w (MLOGP) :	0.77
Log Po/w (SILICOS-IT) :	0.19
Consensus Log Po/w :	1.79

Druglikeness

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

Water Solubility

Log S (ESOL) :	-2.63
Solubility :	0.66 mg/ml ; 0.00232 mol/l
Class :	Soluble
Log S (Ali) :	-3.11
Solubility :	0.223 mg/ml ; 0.000783 mol/l
Class :	Soluble
Log S (SILICOS-IT) :	-2.3
Solubility :	1.42 mg/ml ; 0.00499 mol/l
Class :	Soluble

Medicinal Chemistry

PAINS :	0.0 alert
Brenk :	1.0 alert
Leadlikeness :	0.0
Synthetic accessibility :	4.07

Safety of [ 942190-60-5 ]

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 [ 942190-60-5 ]

* 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.

Upstream synthesis route of [ 942190-60-5 ]
Downstream synthetic route of [ 942190-60-5 ]

[ 942190-60-5 ] Synthesis Path-Upstream 1~4

1
[ 7677-24-9 ]
[ 101385-93-7 ]
[ 1194376-31-2 ]
[ 942190-60-5 ]

Yield	Reaction Conditions	Operation in experiment
32.6%	With potassium cyanide; 18-crown-6 ether In dichloromethane at 0 - 20℃; for 16 h;	Intermediate: tert-butyl 3-cyano-3-hydroxypyrrolidine-1-carboxylate To a solution of tert-butyl 3-oxopyrrolidine-1-carboxylate (1 g, 5.40 mmol) in DCM (10 mL) was added trimethylsilyl cyanide (0.724 mL, 5.40 mmol), KCN (0.035 g, 0.540 mmol) and 18-CROWN-6 (0.143 g, 0.540 mmol) at 0° C. The reaction mixture was warmed to rt and stirred at rt for 16 h. The reaction mixture was cooled to 0° C., and quenched with sat. NaHCO₃, then diluted with EtOAc. The organic phase was separated, washed with sat. NaCl, dried over anhydrous Na₂SO₄, filtered and concentrated. The residue was purified on silica gel chromatography (0-100percent EtOAc/hex) to yield tert-butyl 3-cyano-3-((trimethylsilyl)oxy)pyrrolidine-1-carboxylate (0.5 g, 1.758 mmol, 32.6percent yield) and tert-butyl 3-cyano-3-hydroxypyrrolidine-1-carboxylate (0.306 g, 1.442 mmol, 26.7percent yield). tert-butyl 3-cyano-3-((trimethylsilyl)oxy)pyrrolidine-1-carboxylate: LC/MS (Cond. N-1): [M+H]⁺ 213.2, RT=4.359 min. ¹H NMR (400 MHz, CHLOROFORM-d) 6 ppm 3.83-3.72 (m, 1H), 3.72-3.43 (m, 3H), 2.33 (q, J=6.8 Hz, 2H), 1.52-1.42 (m, 9H), 0.19-0.10 (m, 9H).

Reference： [1] Patent: US2017/107202, 2017, A1, . Location in patent: Paragraph 0452; 0453; 0454; 0455

2
[ 7677-24-9 ]
[ 151-50-8 ]
[ 101385-93-7 ]
[ 942190-60-5 ]

Yield	Reaction Conditions	Operation in experiment
81%	With 18-crown-6 ether In dichloromethane at 0 - 20℃;	To a solution of 3-oxo-pyrrolidine-1 -carboxylic acid tert-butyl ester 1W (10 g, 52.3 mmol) in CH₂CI₂ (150 ml) at 0 ⁰C was added trimethylsilyl cyanide (8.5ml, 63.6 mmol), potassium cyanide (0.34 g, 5.23 mmol) and 18-crown-6 (1.38 g, 5.23 mmol). The reaction mixture was brought to room temperature and stirred overnight. The <n="442"/>reacton mixture was cooled to 0 °C and quenched with saturated NaHCO₃ (200 ml).The organic layer was separated, dried over Na2SO₄, filtered and concentrated. The . -residue wa^DJjriSed on silica, αel elutinα with 1/8 EtOAc/hexane to αive the desired product 2W (2 g, 81percent).

Reference： [1] Patent: WO2007/70398, 2007, A1, . Location in patent: Page/Page column 439

3
[ 7677-24-9 ]
[ 101385-93-7 ]
[ 942190-60-5 ]

Reference： [1] Patent: WO2010/42850, 2010, A1, . Location in patent: Page/Page column 51; 59
[2] Patent: WO2011/44538, 2011, A1, . Location in patent: Page/Page column 97
[3] Patent: WO2009/67692, 2009, A1, . Location in patent: Page/Page column 44; 146
[4] Patent: WO2010/42851, 2010, A1, . Location in patent: Page/Page column 51; 59

4
[ 7677-24-9 ]
[ 101385-93-7 ]
[ 1194376-31-2 ]
[ 942190-60-5 ]

Yield	Reaction Conditions	Operation in experiment
32.6%	With potassium cyanide; 18-crown-6 ether In dichloromethane at 0 - 20℃; for 16 h;	Intermediate: tert-butyl 3-cyano-3-hydroxypyrrolidine-1-carboxylate To a solution of tert-butyl 3-oxopyrrolidine-1-carboxylate (1 g, 5.40 mmol) in DCM (10 mL) was added trimethylsilyl cyanide (0.724 mL, 5.40 mmol), KCN (0.035 g, 0.540 mmol) and 18-CROWN-6 (0.143 g, 0.540 mmol) at 0° C. The reaction mixture was warmed to rt and stirred at rt for 16 h. The reaction mixture was cooled to 0° C., and quenched with sat. NaHCO₃, then diluted with EtOAc. The organic phase was separated, washed with sat. NaCl, dried over anhydrous Na₂SO₄, filtered and concentrated. The residue was purified on silica gel chromatography (0-100percent EtOAc/hex) to yield tert-butyl 3-cyano-3-((trimethylsilyl)oxy)pyrrolidine-1-carboxylate (0.5 g, 1.758 mmol, 32.6percent yield) and tert-butyl 3-cyano-3-hydroxypyrrolidine-1-carboxylate (0.306 g, 1.442 mmol, 26.7percent yield). tert-butyl 3-cyano-3-((trimethylsilyl)oxy)pyrrolidine-1-carboxylate: LC/MS (Cond. N-1): [M+H]⁺ 213.2, RT=4.359 min. ¹H NMR (400 MHz, CHLOROFORM-d) 6 ppm 3.83-3.72 (m, 1H), 3.72-3.43 (m, 3H), 2.33 (q, J=6.8 Hz, 2H), 1.52-1.42 (m, 9H), 0.19-0.10 (m, 9H).

Reference： [1] Patent: US2017/107202, 2017, A1, . Location in patent: Paragraph 0452; 0453; 0454; 0455

[ 942190-60-5 ] Synthesis Path-Downstream 1~4

1
[ 7677-24-9 ]
[ 151-50-8 ]
[ 101385-93-7 ]
[ 942190-60-5 ]

Yield	Reaction Conditions	Operation in experiment
81%	With 18-crown-6 ether In dichloromethane at 0 - 20℃;	37.1 To a solution of 3-oxo-pyrrolidine-1 -carboxylic acid tert-butyl ester 1W (10 g, 52.3 mmol) in CH2CI2 (150 ml) at 0 0C was added trimethylsilyl cyanide (8.5ml, 63.6 mmol), potassium cyanide (0.34 g, 5.23 mmol) and 18-crown-6 (1.38 g, 5.23 mmol). The reaction mixture was brought to room temperature and stirred overnight. The reacton mixture was cooled to 0 °C and quenched with saturated NaHCO3 (200 ml).The organic layer was separated, dried over Na2SO4, filtered and concentrated. The . -residue wa^DJjriSed on silica, αel elutinα with 1/8 EtOAc/hexane to αive the desired product 2W (2 g, 81%).

Reference： [1]Current Patent Assignee: MERCK & CO INC - WO2007/70398, 2007, A1 Location in patent: Page/Page column 439

2
[ 7677-24-9 ]
[ 101385-93-7 ]
[ 942190-60-5 ]

Yield	Reaction Conditions	Operation in experiment
	With zinc(II) iodide In tetrahydrofuran at 20℃; for 24h;	N-Boc-3-pyrrolidone (0.010 mmol) was submitted to Procedure 9 to yield the desired N-Boc-S-hydroxy-pyrrolidine-S-carboxylic acid.N-Boc-l-amino-but-3-ene3-Buten-l -amine (4.93 g, 0.069 mol) was submitted to Procedure 7 for Boc protection to yield a crude, which was purified by flash chromatography (silica gel/hexanes: ethyl acetate 0-30%) to yield N-Boc-l-amino-but-3-ene (6.47 g, 0.038 mol, 55.1 % yield).; Procedure 9: General Procedure for Synthesis of α-hydroxy carboxylic acidsStep No. 1. O-(Trimethylsilyl) cyanohydrines: A 50-mL flask equipped with a magnetic stirring bar and drying tube was charged with the ketone or aldehyde (0.010 mmol), followed by THF (50 mL), trimethylsilyl cyanide (1.39 g, 14 mmol), and zinc iodide (0.090 g, 0.28 mmol), and the reaction mixture was stirred at room temperature for 24 hr. Solvent evaporation gave a residue, which was dissolved in EtOAc (60 mL), washed with 5% aq. NaHCO3 (2 x 30 mL), H2O (30 mL), and brine (30 mL), dried over Na2SO4, filtered and concentrated to dryness to yield a crude, which was carried through to the next step without further purification.
	In tetrahydrofuran at 20℃; for 24h;	N-Boc-3-pyrrolidone (0.010 mmol) was submitted to Procedure 9 to yield the desired N-Boc-3 -hydroxy-pyrrolidine-3 -carboxylic acid.
	With zinc(II) iodide In tetrahydrofuran at 20℃; for 24h;	34 Example 34 6'-(2-Hydroxy-ethyl)-l-(3-hydroxy-pyrrolidin-3-yl-acetyl)-sisomicinN-Boc-S-hydroxypyrrolidine-S-carboxylic acidN-Boc-3-pyrrolidone (0.010 mmol) was submitted to Procedure 15 to yield the desired N-Boc-S-hydroxy-pyrrolidine-S-carboxylic acid. Procedure 15: General Procedure for Synthesis of α-hydroxy carboxylic acidsStep No. 1. O-fTrimethylsilyl) cyanohydrines: A 50-mL flask equipped with a magnetic stirring bar and drying tube was charged with the ketone or aldehyde (0.010 mmol), followed by THF (50 mL), trimethylsilyl cyanide (1.39 g, 14 mmol), and zinc iodide (0.090 g, 0.28 mmol), and the reaction mixture was stirred at room temperature for 24 hr. Solvent evaporation gave a residue, which was dissolved in EtOAc (60 mL), washed with 5% aq. NaHCO3 (2 x 30 mL), H2O (30 mL), and brine (30 mL), dried over Na2SO4, filtered and concentrated to dryness to yield a crude, which was carried through to the next step without further purification.

With zinc(II) iodide In tetrahydrofuran at 20℃; for 24h;

9.1 N-Boc-3-pyrrolidone (0.010 mmol) was submitted to Procedure 9 to yield the desired N-Boc-S-hydroxy-pyrrolidine-S-carboxylic acid.; Procedure 9: General Procedure for Synthesis of α-hydroxy carboxylic acidsStep No. 1. O-(Trimethylsilyl) cyanohydrines: A 50-mL flask equipped with a magnetic stirring bar and drying tube was charged with the ketone or aldehyde (0.010 mmol), followed by THF (50 mL), trimethylsilyl cyanide (1.39 g, 14 mmol), and zinc iodide (0.090 g, 0.28 mmol), and the reaction mixture was stirred at room temperature for 24 hr. Solvent evaporation gave a residue, which was dissolved in EtOAc (60 mL), washed with 5% aq. NaHCO3 (2 x 30 mL), H2O (30 mL), and brine (30 mL), dried over Na2SO4, filtered and concentrated to dryness to yield a crude, which was carried through to the next step without further purification.

Reference： [1]Current Patent Assignee: ACHAOGEN INC - WO2010/42850, 2010, A1 Location in patent: Page/Page column 51; 59
[2]Current Patent Assignee: ACHAOGEN INC - WO2011/44538, 2011, A1 Location in patent: Page/Page column 97
[3]Current Patent Assignee: CIPLA LTD - WO2009/67692, 2009, A1 Location in patent: Page/Page column 44; 146
[4]Current Patent Assignee: ACHAOGEN INC - WO2010/42851, 2010, A1 Location in patent: Page/Page column 51; 59

3
[ 942190-60-5 ]
[ 75315-60-5 ]

Yield	Reaction Conditions	Operation in experiment
	With hydrogenchloride; water; acetic acid Reflux;	N-Boc-3-pyrrolidone (0.010 mmol) was submitted to Procedure 9 to yield the desired N-Boc-S-hydroxy-pyrrolidine-S-carboxylic acid.N-Boc-l-amino-but-3-ene3-Buten-l -amine (4.93 g, 0.069 mol) was submitted to Procedure 7 for Boc protection to yield a crude, which was purified by flash chromatography (silica gel/hexanes: ethyl acetate 0-30%) to yield N-Boc-l-amino-but-3-ene (6.47 g, 0.038 mol, 55.1 % yield).; Step No. 2. Acid hydrolysis to α-hydroxy carboxylic acid: AcOH (25 ml) and cone. HCl (25 ml) were added to the unpurified material from step No.1 and the reaction mixture was refluxed for 2-3 hr. The reaction mixture was then concentrated to dryness to give a white solid, which was carried through to the next step without further purification.
	With hydrogenchloride; water In acetic acid Reflux;	N-Boc-3-pyrrolidone (0.010 mmol) was submitted to Procedure 9 to yield the desired N-Boc-3 -hydroxy-pyrrolidine-3 -carboxylic acid.
	With hydrogenchloride; water; acetic acid for 2 - 3h; Heating / reflux;	34 Example 34 6'-(2-Hydroxy-ethyl)-l-(3-hydroxy-pyrrolidin-3-yl-acetyl)-sisomicin; N-Boc-S-hydroxypyrrolidine-S-carboxylic acidN-Boc-3-pyrrolidone (0.010 mmol) was submitted to Procedure 15 to yield the desired N-Boc-S-hydroxy-pyrrolidine-S-carboxylic acid.; Step No. 2. Acid hydrolysis to α-hydroxy carboxylic acid: AcOH (25 ml) and cone. HCl (25 ml) were added to the unpurifed material from step No.1 and the reaction mixture was refluxed for 2-3 hr. The reaction mixture was then concentrated to dryness to give a white solid, which was carried through to the next step without further purification.

With hydrogenchloride; water; acetic acid Reflux;

9.2 N-Boc-3-pyrrolidone (0.010 mmol) was submitted to Procedure 9 to yield the desired N-Boc-S-hydroxy-pyrrolidine-S-carboxylic acid.; Step No. 2. Acid hydrolysis to α-hydroxy carboxylic acid: AcOH (25 ml) and cone. HCl (25 ml) were added to the unpurified material from step No.1 and the reaction mixture was refluxed for 2-3 hr. The reaction mixture was then concentrated to dryness to give a white solid, which was carried through to the next step without further purification.

4
[ 7677-24-9 ]
[ 101385-93-7 ]
[ 1194376-31-2 ]
[ 942190-60-5 ]

Yield	Reaction Conditions	Operation in experiment
26.7%; 32.6%	With potassium cyanide; 18-crown-6 ether; In dichloromethane; at 0 - 20℃; for 16h;	Intermediate: tert-butyl 3-cyano-3-hydroxypyrrolidine-1-carboxylate To a solution of tert-butyl 3-oxopyrrolidine-1-carboxylate (1 g, 5.40 mmol) in DCM (10 mL) was added trimethylsilyl cyanide (0.724 mL, 5.40 mmol), KCN (0.035 g, 0.540 mmol) and 18-CROWN-6 (0.143 g, 0.540 mmol) at 0 C. The reaction mixture was warmed to rt and stirred at rt for 16 h. The reaction mixture was cooled to 0 C., and quenched with sat. NaHCO3, then diluted with EtOAc. The organic phase was separated, washed with sat. NaCl, dried over anhydrous Na2SO4, filtered and concentrated. The residue was purified on silica gel chromatography (0-100% EtOAc/hex) to yield tert-butyl 3-cyano-3-((trimethylsilyl)oxy)pyrrolidine-1-carboxylate (0.5 g, 1.758 mmol, 32.6% yield) and tert-butyl 3-cyano-3-hydroxypyrrolidine-1-carboxylate (0.306 g, 1.442 mmol, 26.7% yield). tert-butyl 3-cyano-3-((trimethylsilyl)oxy)pyrrolidine-1-carboxylate: LC/MS (Cond. N-1): [M+H]+ 213.2, RT=4.359 min. 1H NMR (400 MHz, CHLOROFORM-d) 6 ppm 3.83-3.72 (m, 1H), 3.72-3.43 (m, 3H), 2.33 (q, J=6.8 Hz, 2H), 1.52-1.42 (m, 9H), 0.19-0.10 (m, 9H).

Reference： [1]Patent: US2017/107202,2017,A1 .Location in patent: Paragraph 0452; 0453; 0454; 0455

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P502	Refer to manufacturer/supplier for information on recovery/recycling

Purity	Size	Price	VIP Price	USA Stock *0-1 Day	Global Stock *5-7 Days	Quantity
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Physical hazards
Code	Phrase
H200	Unstable explosive
H201	Explosive; mass explosion hazard
H202	Explosive; severe projection hazard
H203	Explosive; fire, blast or projection hazard
H204	Fire or projection hazard
H205	May mass explode in fire
H220	Extremely flammable gas
H221	Flammable gas
H222	Extremely flammable aerosol
H223	Flammable aerosol
H224	Extremely flammable liquid and vapour
H225	Highly flammable liquid and vapour
H226	Flammable liquid and vapour
H227	Combustible liquid
H228	Flammable solid
H229	Pressurized container: may burst if heated
H230	May react explosively even in the absence of air
H231	May react explosively even in the absence of air at elevated pressure and/or temperature
H240	Heating may cause an explosion
H241	Heating may cause a fire or explosion
H242	Heating may cause a fire
H250	Catches fire spontaneously if exposed to air
H251	Self-heating; may catch fire
H252	Self-heating in large quantities; may catch fire
H260	In contact with water releases flammable gases which may ignite spontaneously
H261	In contact with water releases flammable gas
H270	May cause or intensify fire; oxidizer
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

[ CAS No. 942190-60-5 ] {[proInfo.proName]}

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[ 942190-60-5 ] Synthesis Path-Upstream 1~4

[ 942190-60-5 ] Synthesis Path-Downstream 1~4

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[ 942190-60-5 ]