1-Pyrrolidinecarboxylic acid, 3-(difluoromethyl)-5-[[[(1,1-dimethylethyl)dimethylsilyl]oxy]methyl]-2-oxo-, phenylmethyl ester, (3S,5S)-

Base Information

Chemical Name:1-Pyrrolidinecarboxylic acid, 3-(difluoromethyl)-5-[[[(1,1-dimethylethyl)dimethylsilyl]oxy]methyl]-2-oxo-, phenylmethyl ester, (3S,5S)-
CAS No.:681283-26-1
Molecular Formula:C20H29F2NO4Si
Molecular Weight:413.537
Hs Code.:

1-Pyrrolidinecarboxylic acid,
3-(difluoromethyl)-5-[[[(1,1-dimethylethyl)dimethylsilyl]oxy]methyl]-2-oxo-,
phenylmethyl ester, (3S,5S)-

Synonyms:

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Business phase:: The product has achieved commercial mass production^*data from LookChem market partment

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Chemical Property of 1-Pyrrolidinecarboxylic acid, 3-(difluoromethyl)-5-[[[(1,1-dimethylethyl)dimethylsilyl]oxy]methyl]-2-oxo-, phenylmethyl ester, (3S,5S)-

Chemical Property:

Purity/Quality:

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Technology Process of 1-Pyrrolidinecarboxylic acid, 3-(difluoromethyl)-5-[[[(1,1-dimethylethyl)dimethylsilyl]oxy]methyl]-2-oxo-, phenylmethyl ester, (3S,5S)-

There total 11 articles about 1-Pyrrolidinecarboxylic acid, 3-(difluoromethyl)-5-[[[(1,1-dimethylethyl)dimethylsilyl]oxy]methyl]-2-oxo-, phenylmethyl ester, (3S,5S)- which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 83.0%

: 501-53-1,94274-21-2
benzyl chloroformate

: 681283-22-7
(5S,3S)-5-tert-butyldimethylsilyloxymethyl-3-difluoromethylpyrrolidin-2-one

: (5S)-N-benzyloxycarbonyl-5-tert-butyldimethylsilyloxymethyl-3-[(Z)-fluoromethylidene]-2-pyrrolidone

: 681283-26-1
(5S,3S)-N-benzyloxycarbonyl-5-tert-butyldimethylsilyloxymethyl-3-difluoromethyl-2-pyrrolidone

Guidance literature:: (5S,3S)-5-tert-butyldimethylsilyloxymethyl-3-difluoromethylpyrrolidin-2-one; With lithium hexamethyldisilazane; In tetrahydrofuran; at -78 ℃; for 0.166667h;

benzyl chloroformate; In tetrahydrofuran; at -78 ℃; for 0.166667h;
DOI:10.1055/s-2004-815932

Reference yield:

: 1499-56-5,775275-31-5,790644-51-8,754962-86-2
(R)-4-hydroxy-L-proline ethyl ester

: 681283-26-1
(5S,3S)-N-benzyloxycarbonyl-5-tert-butyldimethylsilyloxymethyl-3-difluoromethyl-2-pyrrolidone

Guidance literature:: Multi-step reaction with 9 steps

1.1: 15.715 g / DMAP; Et₃N / CH₂Cl₂ / 20 °C

2.1: 11 g / oxalyl chloride; DMSO; Et₃N / CH₂Cl₂ / 2 h / -78 °C

3.1: HMPT / tetrahydrofuran / 0.5 h / 20 °C

3.2: 50 percent / Zn; HMPT / tetrahydrofuran / 0.33 h / Heating

4.1: 94 percent / H₂ / Pd/C / ethanol / 20 °C / 760 Torr

5.1: 68 percent / aq. NaIO₄ / RuO₂*xH₂O / ethyl acetate / 30 h / 20 °C

6.1: CF₃COOH / CH₂Cl₂ / 20 °C

7.1: NaBH₄ / methanol / 2 h / 0 °C

8.1: 587 mg / DMAP; imidazole / CH₂Cl₂; dimethylformamide / 20 °C

9.1: LHMDS / tetrahydrofuran / 0.17 h / -78 °C

9.2: 83 percent / tetrahydrofuran / 0.17 h / -78 °C

With 1H-imidazole; N,N,N,N,N,N-hexamethylphosphoric triamide; dmap; sodium tetrahydroborate; sodium periodate; oxalyl dichloride; hydrogen; dimethyl sulfoxide; triethylamine; trifluoroacetic acid; lithium hexamethyldisilazane; ruthenium(IV) oxide; palladium on activated charcoal; In tetrahydrofuran; methanol; ethanol; dichloromethane; ethyl acetate; N,N-dimethyl-formamide; 2.1: Swern oxidation;
DOI:10.1055/s-2004-815932

Reference yield:

: 74844-91-0
1-tert-butyl 2-methyl (2S,4R)-4-hydroxy-1,2-pyrrolidinedicarboxylate

: 681283-26-1
(5S,3S)-N-benzyloxycarbonyl-5-tert-butyldimethylsilyloxymethyl-3-difluoromethyl-2-pyrrolidone

Guidance literature:: Multi-step reaction with 8 steps

1.1: 11 g / oxalyl chloride; DMSO; Et₃N / CH₂Cl₂ / 2 h / -78 °C

2.1: HMPT / tetrahydrofuran / 0.5 h / 20 °C

2.2: 50 percent / Zn; HMPT / tetrahydrofuran / 0.33 h / Heating

3.1: 94 percent / H₂ / Pd/C / ethanol / 20 °C / 760 Torr

4.1: 68 percent / aq. NaIO₄ / RuO₂*xH₂O / ethyl acetate / 30 h / 20 °C

5.1: CF₃COOH / CH₂Cl₂ / 20 °C

6.1: NaBH₄ / methanol / 2 h / 0 °C

7.1: 587 mg / DMAP; imidazole / CH₂Cl₂; dimethylformamide / 20 °C

8.1: LHMDS / tetrahydrofuran / 0.17 h / -78 °C

8.2: 83 percent / tetrahydrofuran / 0.17 h / -78 °C

With 1H-imidazole; N,N,N,N,N,N-hexamethylphosphoric triamide; dmap; sodium tetrahydroborate; sodium periodate; oxalyl dichloride; hydrogen; dimethyl sulfoxide; triethylamine; trifluoroacetic acid; lithium hexamethyldisilazane; ruthenium(IV) oxide; palladium on activated charcoal; In tetrahydrofuran; methanol; ethanol; dichloromethane; ethyl acetate; N,N-dimethyl-formamide; 1.1: Swern oxidation;
DOI:10.1055/s-2004-815932