143878-87-9|(2S,3S)-Methyl 2-methylpyrrolidine-3-carboxylate| Ambeed

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Quality Control of [ 143878-87-9 ] Purity: 98% SDS Specification

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Product Details of [ 143878-87-9 ]

CAS No. :	143878-87-9
Formula :	C₇H₁₃NO₂
M.W :	143.18
SMILES Code :	O=C([C@@H]1[C@H](C)NCC1)OC
InChI Key :	XQMDYEQHVQBQMQ-WDSKDSINSA-N
Pubchem ID :	10855575

Safety of [ 143878-87-9 ]

GHS Pictogram:
Signal Word:	Warning
Hazard Statements:	H302-H315-H319-H335
Precautionary Statements:	P261-P305+P351+P338

Application In Synthesis of [ 143878-87-9 ]

* 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 [ 143878-87-9 ]

[ 143878-87-9 ] Synthesis Path-Downstream 1~19

1
[ 143878-86-8 ]
[ 143878-87-9 ]

Yield	Reaction Conditions	Operation in experiment
	With hydrogen; acetic acid;palladium 10% on activated carbon; In methanol; for 4.0h;	Example 153 (Preparation of Compound 156) A mixture of methyl (2S,3S)-2-methyl-1-[(1S)-1-phenylethyl]pyrrolidine-3-carboxylate (1.00 g), methanol (20 mL), acetic acid (1.0 mL),and 10% palladium carbon (containing water) (350 mg) was stirred under hydrogen atmosphere for 4 hours. The catalyst was filtered off, the filtrate was concentrated and dried. To the residue was added 4-fluoro-1-naphthonitrile (680 mg), potassium carbonate (1.66 g) and dimethylsulfoxide (10.0 mL), and the mixture was stirred at 100C for 1.5 hours. After cooling to room temperature, water was poured into the reactant and extracted with ethyl acetate. The extracts were washed with water, dried and concentrated. The obtained residue was purified by silica gel column chromatography to obtain methyl (2S,3S)-1-(4-cyano-1-naphthyl)-2-methylpyrrolidine-3-carboxylate (262 mg) (Compound 156). [alpha]D=-236.3 (c=0.408, MeOH). 1H-NMR (200 MHz, CDCl3) delta: 1.35(3H, d, J=6.4 Hz), 2.00-2.52 (2H, m), 3.10-3.48 (2H, m), 3.76 (1H, s), 4.05-4.45 (2H, m), 6.93 (1H, d, J=8.6 Hz), 7.50-7.70 (2H, m), 7.80 (1H, d, J=8.0 Hz), 8.14-8.28 (2H, m). IR (KBr) 2213, 1737, 1570 cm-1
830 mg	With palladium 10% on activated carbon; hydrogen; In methanol; at 20.0℃; for 24.0h;	(2S,3S)-methyl 2-methyl-l-((S)-l-phenylethyl)pyrrolidine-3-carboxylate (1.9 g, 7.68 mmol) was dissolved in methanol (50 mL). This was added to Pd/C (10% / 0.82 g, 0.77 mmol) under nitrogen. The mixture was stirred under a hydrogen atmosphere at room temperature for 24 hours._The resulting mixture was filtered over a dicalite plug and rinsed using of methanol (100 mL). The filtrate was concentrated in vacuo yielding methyl (2S,3S)-2-methylpyrrolidine-3-carboxylate (830 mg) as a clear oil. Ethyl 2-chloro-2-oxo- acetate (1.3 mL, 11.59 mmol) was added drop wise to a solution of methyl (2S,3S)-2- methylpyrrolidine-3-carboxylate (0.83 g, 5.8 mmol) and diisopropylethylamine (4.99 mL, 28.98 mmol) in dry dichloromethane (5 mL) at room temperature. The reaction mixture was stirred at room temperature for 1 h. Saturated aqueous NaHC03 (5 mL) were added to the reaction mixture and the layers were separated. Then it was extracted using dichloromethane (2 X 10 mL). The combined extracts were dried on Na2S04, filtered and concentrated in vacuo. The obtained crude was purified by silica gel column chromatography using gradient elution from heptane to EtOAc. (100:0 to 0: 100). The desired fractions were concentrated in vacuo yielding methyl (2S,3S)-l-(2-ethoxy-2-oxo-acetyl)-2-methyl-pyrrolidine-3-carboxylate (890 mg) of as a yellow oil. methyl (2S,3S)-l-(2-ethoxy-2-oxo-acetyl)-2-methyl-pyrrolidine-3-carboxylate (250 mg, 1 mmol) was dissolved in ethanol (10 mL) and isopropylamine (1698 mu, 19.94 mmol) and the mixture was stirred at 60C for 2 hours. The mixture was concentrated in vacuo. The obtained oil was purified by silica gel column chromatography using gradient elution from heptane to EtOAc. (100:0 to 0: 100). The desired fractions were concentrated under reduced pressure yielding methyl (2S)-l-[2-(isopropylamino)-2-oxo-acetyl]-2-methyl- pyrrolidine-3-carboxylate (380 mg) as a clear oil which was used as such. Methyl (2S)-l-[2-(isopropylamino)-2-oxo-acetyl]-2-methyl-pyrrolidine-3-carboxylate (0.38 g, 1.48 mmol) was dissolved in tetrahydrofuran (10 mL) and this was stirred at room temperature. To this was added LiOH (178mg, 7.41 mmol) in water (2 mL) followed by methanol (2 mL). The resulting mixture was stirred at room temperature for 2 hours. Then, HC1 (1M in H20) (7.41 mL, 1 M, 7.41 mmol) was added and the mixture was concentrated in vacuo until only water remained. Water (5 mL) was added and this solution was extracted using 2-methyl-tetrahydrofuran (3 x 15 mL). The combined extracts were washed with brine (15 mL), dried on Na2S04, filtered and concentrated in vacuo yielding (2S)- 1 -[2-(isopropylamino)-2-oxo-acetyl]-2-methyl-pyrrolidine-3-carboxylic acid (312 mg) which was used as such. (2S)- 1 -[2-(isopropylamino)-2-oxo-acetyl]-2-methyl-pyrrolidine-3-carboxylic acid (104 mg, 0.43 mmol) was dissolved in Nu,Nu-dimethylformamide (1 mL). Then HATU (0.18 g, 0.47 mmol) was added and this mixture was stirred for 20 minutes. Then DIPEA (0.22 mL, 0.75 g/mL, 1.29 mmol) was added folowed by 5-amino-2-fluorobenzonitrile (0.12 g, 0.86 mmol). The reaction mixture was stirred at 50C for 4 hours. Then this mixture was cooled to room temperature and injected directly onto a silica plug. The mixture was purified by silica gel column chromatography using gradient elution from heptane to EtOAc. (100:0 to 0: 100) and further by preperative HPLC (Stationary phase: RP SunFire Prep C18 OBD-IotaOmicronmuiotaeta, 30x150mm, Mobile phase: 0.25% NH4HC03 solution in water, MeOH) The desired fractions were concentrated under reduced pressure and co- evaporated twice with methanol (2 X 15mL) and dried in a vacuum oven at 55C for 18 hours yielding compound 27 (57 mg) as a white powder. Method B, Rt = 0.81 (31 %) and 0.83 min (69 %), m/z = 359.2 (M-H)~, Exact mass: 360.2
	With palladium 10% on activated carbon; hydrogen; In methanol; at 20.0℃; under 21979.4 Torr; for 16.0h;	Step d. A solution of methyl (2S,3S)-2-methyl-l-((S)-l-phenylethyl)pyrrolidine-3- carboxylate (137 mmol) in MeOH (700 ml) was charged in an autoclave vessel at rt under nitrogen atmosphere. 10% Pd/C (0.3% w/w) was added to the reaction mixture at rt under nitrogen atmosphere The resulting reaction mixture was stirred in the autoclave at rt under 425 psi H2 pressure for 16 h. The resulting reaction mixture was carefully filtered through celite hyflow and concentrated under reduced pressure to yield methyl (2S,3S)-2- methylpyrrolidine-3-carboxylate (quantitative). The material was immediately used for the next step. MS: ES+ 144.05; *H NMR (400 MHz, DMSO-d6) delta ppm 3.59 (s, 3 H), 3.18 - 3.25 (m, 1 H), 2.96 - 3.02 (m, 1 H), 2.82 - 2.88 (m, 1 H), 2.61 - 2.66 (m, 1 H), 1.80 - 1.97 (m, 2 H), 0.94 (d, J=6.714 Hz, 3 H).

References: [1]Tetrahedron Letters,1992,vol. 33,p. 4311 - 4312.
[2]Patent: EP1553074,2005,A1 .Location in patent: Page/Page column 99.
[3]Patent: WO2015/59212,2015,A1 .Location in patent: Page/Page column 39; 40.
[4]Patent: WO2016/46530,2016,A1 .Location in patent: Page/Page column 60.

2
[ 143955-12-8 ]
[ 143878-87-9 ]

References: [1]Tetrahedron Letters,1992,vol. 33,p. 4311 - 4312.

3
[ 143878-85-7 ]
[ 143878-87-9 ]

References: [1]Tetrahedron Letters,1992,vol. 33,p. 4311 - 4312.
[2]Patent: WO2015/59212,2015,A1 .
[3]Patent: WO2016/46530,2016,A1 .

4
[ 143878-87-9 ]
(2S)-N-(3-cyano-4-fluorophenyl)-1-[2-(isopropylamino)-2-oxoacetyl]-2-methylpyrrolidine-3-carboxamide [ No CAS ]

References: [1]Patent: WO2015/59212,2015,A1 .

5
[ 143878-87-9 ]
methyl (2S)-1-[2-(isopropylamino)-2-oxoacetyl]-2-methylpyrrolidine-3-carboxylate [ No CAS ]

References: [1]Patent: WO2015/59212,2015,A1 .

6
[ 143878-87-9 ]
(2S)-1-[2-(isopropylamino)-2-oxoacetyl]-2-methylpyrrolidine-3-carboxylic acid [ No CAS ]

References: [1]Patent: WO2015/59212,2015,A1 .

7
[ 143878-87-9 ]
(2S,3R)-N-(3-chloro-4,5-difluorophenyl)-2-methyl-1-[2-oxo-2-[(1R)-(2,2,2-trifluoro-1-methylethyl)amino]acetyl]pyrrolidine-3-carboxamide [ No CAS ]
(2S,3S)-N-(3-chloro-4,5-difluorophenyl)-2-methyl-1-[2-oxo-2-[(1R)-(2,2,2-trifluoro-1-methylethyl)amino]acetyl]pyrrolidine-3-carboxamide [ No CAS ]

References: [1]Patent: WO2015/59212,2015,A1 .

8
[ 143878-87-9 ]
2-[(2S,3S)-3-methoxycarbonyl-2-methylpyrrolidin-1-yl]-2-oxoacetic acid [ No CAS ]

References: [1]Patent: WO2015/59212,2015,A1 .

9
[ 143878-87-9 ]
methyl (2S,3S)-2-methyl-1-[2-oxo-2-[[(1R)-2,2,2-trifluoro-1-methylethyl]amino]acetyl]pyrrolidine-3-carboxylate [ No CAS ]

References: [1]Patent: WO2015/59212,2015,A1 .

10
[ 143878-87-9 ]
(2S,3S)-2-methyl-1-[2-oxo-2-[[(1R)-2,2,2-trifluoro-1-methylethyl]amino]acetyl]pyrrolidine-3-carboxylic acid [ No CAS ]

References: [1]Patent: WO2015/59212,2015,A1 .

11
[ 4755-77-5 ]
[ 143878-87-9 ]
methyl (2S,3S)-1-(2-ethoxy-2-oxoacetyl)-2-methylpyrrolidine-3-carboxylate [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
890 mg	With N-ethyl-N,N-diisopropylamine; In dichloromethane; at 20.0℃;	(2S,3S)-methyl 2-methyl-l-((S)-l-phenylethyl)pyrrolidine-3-carboxylate (1.9 g, 7.68 mmol) was dissolved in methanol (50 mL). This was added to Pd/C (10% / 0.82 g, 0.77 mmol) under nitrogen. The mixture was stirred under a hydrogen atmosphere at room temperature for 24 hours._The resulting mixture was filtered over a dicalite plug and rinsed using of methanol (100 mL). The filtrate was concentrated in vacuo yielding <strong>[143878-87-9]methyl (2S,3S)-2-methylpyrrolidine-3-carboxylate</strong> (830 mg) as a clear oil. Ethyl 2-chloro-2-oxo- acetate (1.3 mL, 11.59 mmol) was added drop wise to a solution of methyl (2S,3S)-2- methylpyrrolidine-3-carboxylate (0.83 g, 5.8 mmol) and diisopropylethylamine (4.99 mL, 28.98 mmol) in dry dichloromethane (5 mL) at room temperature. The reaction mixture was stirred at room temperature for 1 h. Saturated aqueous NaHC03 (5 mL) were added to the reaction mixture and the layers were separated. Then it was extracted using dichloromethane (2 X 10 mL). The combined extracts were dried on Na2S04, filtered and concentrated in vacuo. The obtained crude was purified by silica gel column chromatography using gradient elution from heptane to EtOAc. (100:0 to 0: 100). The desired fractions were concentrated in vacuo yielding methyl (2S,3S)-l-(2-ethoxy-2-oxo-acetyl)-2-methyl-pyrrolidine-3-carboxylate (890 mg) of as a yellow oil. methyl (2S,3S)-l-(2-ethoxy-2-oxo-acetyl)-2-methyl-pyrrolidine-3-carboxylate (250 mg, 1 mmol) was dissolved in ethanol (10 mL) and isopropylamine (1698 mu, 19.94 mmol) and the mixture was stirred at 60C for 2 hours. The mixture was concentrated in vacuo. The obtained oil was purified by silica gel column chromatography using gradient elution from heptane to EtOAc. (100:0 to 0: 100). The desired fractions were concentrated under reduced pressure yielding methyl (2S)-l-[2-(isopropylamino)-2-oxo-acetyl]-2-methyl- pyrrolidine-3-carboxylate (380 mg) as a clear oil which was used as such. Methyl (2S)-l-[2-(isopropylamino)-2-oxo-acetyl]-2-methyl-pyrrolidine-3-carboxylate (0.38 g, 1.48 mmol) was dissolved in tetrahydrofuran (10 mL) and this was stirred at room temperature. To this was added LiOH (178mg, 7.41 mmol) in water (2 mL) followed by methanol (2 mL). The resulting mixture was stirred at room temperature for 2 hours. Then, HC1 (1M in H20) (7.41 mL, 1 M, 7.41 mmol) was added and the mixture was concentrated in vacuo until only water remained. Water (5 mL) was added and this solution was extracted using 2-methyl-tetrahydrofuran (3 x 15 mL). The combined extracts were washed with brine (15 mL), dried on Na2S04, filtered and concentrated in vacuo yielding (2S)- 1 -[2-(isopropylamino)-2-oxo-acetyl]-2-methyl-pyrrolidine-3-carboxylic acid (312 mg) which was used as such. (2S)- 1 -[2-(isopropylamino)-2-oxo-acetyl]-2-methyl-pyrrolidine-3-carboxylic acid (104 mg, 0.43 mmol) was dissolved in Nu,Nu-dimethylformamide (1 mL). Then HATU (0.18 g, 0.47 mmol) was added and this mixture was stirred for 20 minutes. Then DIPEA (0.22 mL, 0.75 g/mL, 1.29 mmol) was added folowed by 5-amino-2-fluorobenzonitrile (0.12 g, 0.86 mmol). The reaction mixture was stirred at 50C for 4 hours. Then this mixture was cooled to room temperature and injected directly onto a silica plug. The mixture was purified by silica gel column chromatography using gradient elution from heptane to EtOAc. (100:0 to 0: 100) and further by preperative HPLC (Stationary phase: RP SunFire Prep C18 OBD-IotaOmicronmuiotaeta, 30x150mm, Mobile phase: 0.25% NH4HC03 solution in water, MeOH) The desired fractions were concentrated under reduced pressure and co- evaporated twice with methanol (2 X 15mL) and dried in a vacuum oven at 55C for 18 hours yielding compound 27 (57 mg) as a white powder. Method B, Rt = 0.81 (31 %) and 0.83 min (69 %), m/z = 359.2 (M-H)~, Exact mass: 360.2

References: [1]Patent: WO2015/59212,2015,A1 .Location in patent: Page/Page column 39; 40.

12
[ 143878-87-9 ]
tert-butyl (2S,3S)-3-((6-(1H-pyrazol-4-yl)isoquinolin-3-yl)carbamoyl)-2-methylpyrrolidine-1-carboxylate [ No CAS ]

References: [1]Patent: WO2016/46530,2016,A1 .

13
[ 143878-87-9 ]
[ 664364-34-5 ]

References: [1]Patent: WO2016/46530,2016,A1 .

14
[ 143878-87-9 ]
(2S,3S)-1-cyano-N-(5-(((R)-2-(methoxymethyl)pyrrolidin-1-yl)methyl)thiazol-2-yl)-2-methylpyrrolidine-3-carboxamide [ No CAS ]

References: [1]Patent: WO2016/46530,2016,A1 .

15
[ 143878-87-9 ]
tert-butyl (2S,3S)-3-((5-(((R)-2-(methoxymethyl)pyrrolidin-1-yl)methyl)thiazol-2-yl)carbamoyl)-2-methylpyrrolidine-1-carboxylate [ No CAS ]

References: [1]Patent: WO2016/46530,2016,A1 .

16
[ 143878-87-9 ]
(2S,3S)-N-(5-(((R)-2-(methoxymethyl)pyrrolidin-1-yl)methyl)thiazol-2-yl)-2-methylpyrrolidine-3-carboxamide trifluoroacetate [ No CAS ]

References: [1]Patent: WO2016/46530,2016,A1 .

17
[ 24424-99-5 ]
[ 143878-87-9 ]
1-(tert-butyl) 3-methyl (2S,3S)-2-methylpyrrolidine-1,3-dicarboxylate [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
111 mmol	With dmap; In tetrahydrofuran; for 16.0h;	Step e. To stirred a solution of <strong>[143878-87-9]methyl (2S,3S)-2-methylpyrrolidine-3-carboxylate</strong> (139 mmol) in THF (200 ml) were added DMAP (8.1 mmol) and BOC anhydride (751 mmol) at 0C. The reaction mixture stirred at 0C for 16 h. The resulting reaction mixture was poured into water (100 ml) and extracted with DCM (2 x 200 ml). The combined organic phase was collected, dried over a2S04, filtered and concentrated under reduced pressure. The resulting residue was purified by column chromatography (10% EtOAc in hexane) yielding l-(tert- butyl) 3-methyl (2S,3S)-2-methylpyrrolidine-l,3-dicarboxylate (111 mmol). MS: ES+ 188 (M-56) 144 (M-100); 1H NMR (400 MHz, DMSO-d6) delta ppm 3.98 - 4.03 (m, 1 H), 3.64 (s, 3 H), 3.30 - 3.41 (m, 1 H), 3.12 - 3.29 (m, 2 H), 2.06 - 2.14 (m, 1 H), 1.91 - 1.99 (m, 1 H), 1.40 (s, 9 H), 0.95 (d, J=6.40 Hz, 3 H).

References: [1]Patent: WO2016/46530,2016,A1 .Location in patent: Page/Page column 60-61.

18
[ 105-45-3 ]
[ 143878-87-9 ]

References: [1]Patent: WO2016/46530,2016,A1 .

19
[ 38806-09-6 ]
[ 143878-87-9 ]

References: [1]Patent: WO2016/46530,2016,A1 .

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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

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CAS No.: 143878-87-9

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CAS No.: 143878-87-9

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[ 143878-87-9 ] Synthesis Path-Downstream 1~19

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