1001353-87-2|(S)-1-(tert-Butoxycarbonyl)-4,4-dimethylpyrrolidine-2-carboxylic acid| Ambeed

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Quality Control of [ 1001353-87-2 ] Purity: 98% SDS Specification

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Product Details of [ 1001353-87-2 ]

CAS No. :	1001353-87-2
Formula :	C₁₂H₂₁NO₄
M.W :	243.30
SMILES Code :	C(C)(C)(C)OC(=O)N1CC(C[C@H]1C(=O)O)(C)C
MDL No. :	MFCD11040193
InChI Key :	ACHKRIQLSCPKKK-QMMMGPOBSA-N
Pubchem ID :	25067306

Safety of [ 1001353-87-2 ]

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

Application In Synthesis of [ 1001353-87-2 ]

* 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 [ 1001353-87-2 ]

[ 1001353-87-2 ] Synthesis Path-Downstream 1~35

1
[ 1001353-86-1 ]
[ 1001353-87-2 ]

Yield	Reaction Conditions	Operation in experiment
91%	With lithium hydroxide; In tetrahydrofuran; methanol; water; at 20℃;	163C. (S)-4,4-Dimethylpyrrolidine-2-carboxylic acid To a solution of (S)-1-tert-butyl 2-ethyl 4,4-dimethylpyrrolidine-1,2-dicarboxylate (1.0 g, 3.7 mmol) in MeOH/H2O/THF (20/15/10 mL) was added lithium hydroxide monohydrate (0.78 g, 18.5 mmol), and the resulting mixture was stirred at room temperature overnight. The solvent was removed and the resulting residue was acidified with phosphoric acid to pH 3. The aqueous layer was extracted with EtOAc, washed with brine, dried over Na2SO4, and filtered. The filtrate was evaporated to furnish the crude product (0.82 g, 91%). 1H NMR (CD3OD, 400 MHz) δ 4.21 (m, 1H), 3.24-3.29 (m, 1H), 3.11-3.14 (m, 1H), 2.08 (m, 1H), 1.75 (m, 1H), 1.40 (s, 9H), 1.11 (s, 3H), and 1.04 (s, 3H).

References: [1]Patent: US2008/9497,2008,A1 .Location in patent: Page/Page column 71.

2
[ 1001353-87-2 ]
4,4-dimethyl-L-proline [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
93%	With trifluoroacetic acid; In dichloromethane; at 20℃; for 4h;	The crude material from above was dissolved in methylene chloride (30 mL), and trifluoroacetic acid (5 mL) was added. The reaction mixture was stirred at room temperature for 4 h. After concentrating to dryness, the residue was passed through a MCX cartridge, the cartridge was eluted with a 2 N solution of ammonia in methanol and removal of the solvents gave (163C) as a solid (450 mg, 93%). 1H NMR (CD3OD, 400 MHz) δ 3.28 (m, 1H), 3.11 (m, 1H), 2.24-2.30 (m, 1H), 1.95-2.00 (m, 1H), 1.17 (s, 3H), and 1.16 (s, 3H).

References: [1]Patent: US2008/9497,2008,A1 .Location in patent: Page/Page column 71.

3
[ 24424-99-5 ]
[ 1001353-87-2 ]

References: [1]Patent: US2008/9497,2008,A1 .
[2]Patent: WO2014/82380,2014,A1 .
[3]Patent: CN103880823,2017,B .

4
(S)-ethyl N-tert-butoxycarbonylpyroglutamate [ No CAS ]
[ 1001353-87-2 ]

References: [1]Patent: US2008/9497,2008,A1 .

5
[ 7149-65-7 ]
[ 1001353-87-2 ]

References: [1]Patent: US2008/9497,2008,A1 .

6
[ 158392-74-6 ]
[ 1001353-87-2 ]

References: [1]Patent: WO2012/39717,2012,A1 .

7
(S)-5-Hydroxy-4,4-dimethyl-pyrrolidine-1,2-dicarboxylic acid 1-tert-butyl ester 2-methyl ester [ No CAS ]
[ 1001353-87-2 ]

References: [1]Patent: WO2012/39717,2012,A1 .

8
[ 138423-86-6 ]
[ 1001353-87-2 ]

Yield	Reaction Conditions	Operation in experiment
95%	With lithium hydroxide monohydrate; In water; at 0 - 20℃; for 2h;Inert atmosphere; Sealed tube;	To a solution of compound 15-2 (4.85 g, 18.86 mmol) in THF (40 mL) was added lithium hydroxide monohydrate aqueous solution (1.5 g, 20 mL) dropwise at 0 C. At the end of the addition, the mixture was stirred at rt for 2.0 hrs. After the reaction was completed, the THF solvent was removed and 50 mL of water was added to the mixture. The resulting mixture was washed with EtOAc (30 mL x 3). The aqueous phase was adjusted to pH 1 with hydrochloric acid (1 M) and extracted with EtOAc (50 mL x 3). The combined organic layers were washed with brine, dried over anhydrous Na2S04 and concentrated in vacuo to give the title compound as a white solid (4.35 g, 95%). The compound was characterized by the following spectroscopic data: MS (ESI, pos.ion) mlz: 244.5 [M+H]+; 'H NMR (400 MHz, CD3OD) δ (ppm): 4.34-4.31 (m, 1H), 3.28-3.22 (m, 1H), 3.20-3.13 (m, 1H), 2.23-2.18 (m, 1H), 1.85-1.80 (m, 1H), 1.46 (s, 9H), 1.01-0.99 (m, 3H), 0.86-0.84 (m, 3H).
95%	With lithium hydroxide monohydrate; In tetrahydrofuran; water; at 0 - 20℃; for 2h;	Compound 10-2 (4.85 g, 18.86 mmol) was dissolved in THF (40 mL) and an aqueouslithium hydroxide monohydrate solution (1.5 g, 20 mL) was added to the system at 0 C.The mixture was reacted at room temperature for 2.0 hours. After completion of thereaction, THF was removed, water (50 mL) was added and the mixture was washed with EtOAc(30 mL × 3). After partitioning, the aqueous layer was adjusted to pH 1 with dilutehydrochloric acid (1 M) The combined organic phases were washed with saturated brine anddried over anhydrous Na 2SO 4Dried and concentrated to give 4.35 g of white solid, yield:95%.
	With water; lithium hydroxide; In ethanol; at 0 - 20℃; for 6h;	Example 14, Step dA solution of proline N14c (500 mg, 1.94 mmol) in EtOH (8 mL) was cooled to 0 C, LiOH (93 mg, 3.89 mmol) in water (4 mL) was added, and the reaction mixture was stirred at RT for 6 h. It was then concentrated under reduced pressure, and the resulting crude material was dissolved in water and extracted with Et20 (20 mL). The aqueous phase was acidified to pH 4 with 1 N HC1 and extracted withEtOAc (100 mL). The organic phase was washed with brine, dried over Na2S04 and concentrated in vacuo to afford acid 14d (454 mg). XH NMR (CDC13, δ = 7.26 ppm, 400 MHz): δ 4.42-4.23 (m, 1H), 3.26 (d, J = 10.8, 1H), 3.10 (d, J = 10.8, 1H), 2.30- 2.20 (m, 1H), 1.96-1.82 (m, 1H), 1.50/1.45 (s, 9H), 1.11/1.07 (s, 6H).

References: [1]Patent: WO2014/82380,2014,A1 .Location in patent: Paragraph 00460; 00462.
[2]Patent: CN103880823,2017,B .Location in patent: Paragraph 1061; 1066; 1067.
[3]Patent: WO2012/39717,2012,A1 .Location in patent: Page/Page column 153.

9
[ 1001353-87-2 ]
[ 99-73-0 ]
[ 1613055-95-0 ]

Yield	Reaction Conditions	Operation in experiment
	With triethylamine; In dichloromethane; at 0 - 20℃; for 2h;Inert atmosphere; Sealed tube;	To a solution of compound 15-3 (3.18 g, 13.1 mmol) and compound 1-12-2 (3.63 g, 13.1 mmol) in DCM (40 mL) was added Et3N (3.9 mL, 26.3 mmol) dropwise at 0 C. At the end of the addition, the mixture was stirred at rt for 2.0 hrs. After the reaction was completed, the mixture was quenched with water (50 mL). The aqueous layer was extracted with DCM (50 mL x 3). The combined organic layers were washed with brine, dried over anhydrous Na2S04 and concentrated in vacuo to give the crude product (3.27 g), which was used for the next step without further purification. The compound was characterized by the following spectroscopic data: MS (ESI, pos.ion) mlz: 413.5 [M+H]+.
	With triethylamine; In dichloromethane; at 0 - 20℃; for 2h;	The compound 10 - 3 (3.18 g, 13.1 mmol) of the compound 3 - 1 - 0 (3.63 g, 13.1 mmol) dissolved in DCM (40 ml) in, 0 C lower, slowly into the Et3 N (3.9 ml, 26.3 mmol), then completing, the reaction at room temperature for 2.0 hours. After the reaction is complete, the addition of water (50 ml) quenching the reaction, the water layer DCM (50 ml × 3) extraction, the combined organic phase, saturated salt water for washing, anhydrous Na2 SO4 Drying, concentrated to obtain the crude product 3.27 g, directly used for the next step reaction.

References: [1]Patent: WO2014/82380,2014,A1 .Location in patent: Paragraph 00460; 00463.
[2]Patent: CN103880823,2017,B .Location in patent: Paragraph 1061; 1070; 1071.

10
4,4-dimethyl-pyrrolidine-2-carboxylic acid methyl ester [ No CAS ]
[ 1001353-87-2 ]

References: [1]Patent: WO2014/82380,2014,A1 .
[2]Patent: CN103880823,2017,B .

11
[ 1001353-87-2 ]
[ 1613055-96-1 ]

References: [1]Patent: WO2014/82380,2014,A1 .
[2]Patent: CN103880823,2017,B .

12
[ 1001353-87-2 ]
[ 1613055-97-2 ]

References: [1]Patent: WO2014/82380,2014,A1 .
[2]Patent: CN103880823,2017,B .

13
[ 1001353-87-2 ]
[ 1613055-98-3 ]

References: [1]Patent: WO2014/82380,2014,A1 .

14
[ 1001353-87-2 ]
[ 1613055-99-4 ]

References: [1]Patent: WO2014/82380,2014,A1 .

15
[ 1001353-87-2 ]
[ 1613056-00-0 ]

References: [1]Patent: WO2014/82380,2014,A1 .

16
[ 1001353-87-2 ]
[ 1613056-01-1 ]

References: [1]Patent: WO2014/82380,2014,A1 .
[2]Patent: WO2014/82380,2014,A1 .

17
[ 1001353-87-2 ]
[ 1575-37-7 ]
C₁₈H₂₆BrN₃O₃ [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
		To a solution of compound 15-3 (2.6 g, 10.7 mmol) and HATU (4.88 g, 12.84 mmol) in THF (30 mL) was added DIPEA (1.95 mL, 11.8 mmol) at 0 C. After stirring at 0 C for 0.5 hr, compound 2-10 (2.22 g, 11.9 mmol) was added in a portionwise manner. At the end of the addition, the mixture was stirred at rt for 4.0 hrs. After the reaction was completed, the mixture was quenched with water (50 mL), the THF solvent was removed, and the resulting mixture was extracted with EtOAc (50 mL x 3). The combined organic layers were washed with brine, dried over anhydrous Na2S04 and concentrated in vacuo. The residue was dissolved in glacial acetic acid (20 mL), and the solution was stirred at 40 C overnight. After the reaction was completed, the mixture was concentrated in vacuo. The residue was dissolved in EtOAc (100 mL). The mixture was washed with Na2C03 aqueous solution (50 mL x 3), dried over anhydrous Na2S04 and concentrated in vacuo. The residue was purified by silica gel column chromatography (PE/EtOAc (v/v) = 1/2) to give the title compound (2.70 g, 65%). The compound was characterized by the following spectroscopic data: MS (ESI, pos.ion) mlz: 395.5 [M+H] ; and NMR (400 MHz, CDC13) δ (ppm): 7.71-7.70 (q, 1H), 7.33, 7.30 (d, d, 1H), 7.20, 7.18 (d, d, 1H), 5.32-5.27 (m, 1H), 3.41-3.34 (m, 1H), 3.30-3.23 (m, 1H), 2.38-2.32 (m, 1H), 2.00-1.94 (m, 1H), 1.41 (s, 9H), 1.01-0.99 (m, 3H), 0.86-0.84 (m, 3H).

References: [1]Patent: WO2014/82380,2014,A1 .Location in patent: Paragraph 00460; 00467.

18
[ 1001353-87-2 ]
C₄₉H₆₆N₈O₆S [ No CAS ]

References: [1]Patent: CN103880823,2017,B .
[2]Patent: CN103880823,2017,B .

19
[ 1001353-87-2 ]
C₃₁H₃₈BrN₃O₂S [ No CAS ]

References: [1]Patent: CN103880823,2017,B .

20
[ 1001353-87-2 ]
C₃₇H₅₀BN₃O₄S [ No CAS ]

References: [1]Patent: CN103880823,2017,B .

21
[ 1001353-87-2 ]
[ 212890-86-3 ]

Yield	Reaction Conditions	Operation in experiment
75%	With borane-THF; In tetrahydrofuran; at 0℃; for 3h;Inert atmosphere;	Compound 10-3 (1.13 g, 4.66 mmol) was dissolved in THF (10 mL) and borane (10mL, 1 M in THF) was slowly added dropwise to the reaction flask under nitrogen at 0 C. . After the reaction was completed, the reaction was quenched with methanol (10 mL).The reaction solution was concentrated and purified by column chromatography (eluent: PE/ EtOAc (v / v) = 3/2) to give 0.8 g of a colorless oil Rate: 75%.
	With borane-THF; In tetrahydrofuran; at 0 - 20℃;	Step 1: Into a 250-mL 3-necked round-bottom flask, was placed (2S)-1-(tert-butoxycarbonyl)- 4,4-dimethylpyrrolidine-2-carboxylic acid (3.9 g, 16.03 mmol, 1.00 equiv), and THF (50.00 mL). This was followed by the addition of BTb-THF (48.06 mL, 48.07 mmol, 3.00 equiv) dropwise with stirring at 0 ?C. The resulting solution was stirred for overnight at room temperature. The reaction was then quenched by the addition of 50 mL of MeOH. The reaction mixture was then heated to reflux for 3 h. The reaction mixture was cooled to room temperature. The resulting mixture was concentrated. The resulting solution was extracted with 3x100 mL of dichloromethane dried over anhydrous sodium sulfate and concentrated. This resulted in tert-butyl (2S)-2-(hydroxymethyl)-4,4-dimethylpyrrolidine-1-carboxylate.

References: [1]Patent: CN103880823,2017,B .Location in patent: Paragraph 1061; 1089; 1090.
[2]Patent: WO2020/72377,2020,A1 .Location in patent: Paragraph 0312.

22
[ 1001353-87-2 ]
[ 1369594-35-3 ]

References: [1]Patent: CN103880823,2017,B .

23
[ 1001353-87-2 ]
[ 1369594-36-4 ]

References: [1]Patent: CN103880823,2017,B .

24
[ 1001353-87-2 ]
C₁₄H₂₁I₂N₃O₂ [ No CAS ]

References: [1]Patent: CN103880823,2017,B .

25
[ 1001353-87-2 ]
C₁₄H₂₂IN₃O₂ [ No CAS ]

References: [1]Patent: CN103880823,2017,B .

26
[ 1001353-87-2 ]
C₄₅H₆₀N₆O₄S [ No CAS ]

References: [1]Patent: CN103880823,2017,B .
[2]Patent: CN103880823,2017,B .

27
[ 1001353-87-2 ]
C₃₅H₄₄N₆S*4ClH [ No CAS ]

References: [1]Patent: CN103880823,2017,B .
[2]Patent: CN103880823,2017,B .

28
[ 1001353-87-2 ]
(S)-4,4-Dimethyl-pyrrolidine-2-carboxylic acid methyl ester; hydrochloride [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	With thionyl chloride; In methanol; at 0 - 20℃; for 3.41667h;	To a solution of 1 (23.7 g, 97.4 mmol, 1.00 eq.) in MeOH (100 mL) was slowly added thionyl chloride (14.2 mL, 195 mmol, 2.00 eq.) at 0 C over 25 mm. The mixture was stirred at room temperature for 3h, then concentrated under reduced pressure. The residue was dissolved in DCM (170 mL) and added Et3N (41 mL, 292 mmol, 3.00 eq.) at 0 C. To the mixture, trityl chloride (27.2 g, 97.4 mmol, 1.00 eq.) was added at 0 C, and the mixture warmed to room temperature and continued stirring for 17 h. The mixture was filtered and washed with DCM (100 mL). Filtrate was washed with saturated NaHCO3 (170 mL2), and back-extracted with DCM (50 mL1). The combined organic layers were dried over Na2SO4, filtered, and concentrated to obtain compound 2 (43.51 g, crude, pale brown oil), which was used directly without further purification.

References: [1]Patent: WO2018/237194,2018,A1 .Location in patent: Paragraph 001409; 001411; 001412; 001413.

29
[ 1001353-87-2 ]
C₂₇H₂₉NO₂ [ No CAS ]

References: [1]Patent: WO2018/237194,2018,A1 .

30
[ 1001353-87-2 ]
C₂₆H₂₉NO [ No CAS ]

References: [1]Patent: WO2018/237194,2018,A1 .

31
[ 1001353-87-2 ]
C₂₆H₂₇NO [ No CAS ]

References: [1]Patent: WO2018/237194,2018,A1 .

32
[ 1001353-87-2 ]
C₄₀H₄₃NOSi [ No CAS ]

References: [1]Patent: WO2018/237194,2018,A1 .

33
[ 1001353-87-2 ]
C₂₁H₂₉NOSi [ No CAS ]

References: [1]Patent: WO2018/237194,2018,A1 .

34
[ 1001353-87-2 ]
tert-butyl (2S)-2-(2-bromo-3-hydroxyphenoxymethyl)-4,4-dimethylpyrrolidine-1-carboxylate [ No CAS ]

References: [1]Patent: WO2020/72377,2020,A1 .

35
[ 1001353-87-2 ]
2-bromo-3-[[(2S)-4,4-dimethylpyrrolidin-2-yl]methoxy]phenol [ No CAS ]

References: [1]Patent: WO2020/72377,2020,A1 .

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Technical Information

• Acyl Group Substitution • Bouveault-Blanc Reduction • Catalytic Hydrogenation • Complex Metal Hydride Reductions • Ester Cleavage • Reactions with Organometallic Reagents • Specialized Acylation Reagents-Carbodiimides and Related Reagents

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P410 + P403	Protect from sunlight. Store in a well-ventilated place.
P410 + P412	Protect from sunlight. Do not expose to temperatures exceeding 50 oC/122oF.
P411 + P235	Keep cool.
Disposal
Code	Phrase
P501	Dispose of contents/container to ...
P502	Refer to manufacturer/supplier for information on recovery/recycling

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

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CAS No.: 1001353-87-2

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CAS No.: 1001353-87-2

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Product Details of [ 1001353-87-2 ]

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Application In Synthesis of [ 1001353-87-2 ]

[ 1001353-87-2 ] Synthesis Path-Downstream 1~35

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