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

Base Information

• Chemical Name: 1-Pyrrolidinecarboxylic acid, 5-[[[(1,1-dimethylethyl)dimethylsilyl]oxy]methyl]-2-oxo-3-(phenylseleno)-, 1,1-dimethylethyl ester, (5S)-
• CAS No.: 293297-95-7
• Molecular Formula: C22H35NO4SeSi
• Molecular Weight: 484.57
• Mol file: 293297-95-7.mol

Synonyms:

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

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

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

There total 13 articles about 1-Pyrrolidinecarboxylic acid, 5-[[[(1,1-dimethylethyl)dimethylsilyl]oxy]methyl]-2-oxo-3-(phenylseleno)-, 1,1-dimethylethyl ester, (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:

(S)-Pyroglutaminol (17342-08-4) → (5S)-N-(tert-Butoxycarbonyl)-5-(((tert-butyldimethylsilyl)oxy)methyl)-3-(phenylseleno)pyrrolidin-2-one (293297-95-7)

Guidance literature:

Multi-step reaction with 3 steps

1.1: 96 percent / imidazole / dimethylformamide / 24 h

2.1: 99 percent / DMAP / acetonitrile / 0 - 20 °C

3.1: LiHMDS / tetrahydrofuran; hexane / 0.25 h / -78 °C

3.2: tetrahydrofuran; hexane / 1 h / -78 °C

With 1H-imidazole; dmap; lithium hexamethyldisilazane; In tetrahydrofuran; hexane; N,N-dimethyl-formamide; acetonitrile;

DOI:10.1016/S0040-4020(01)00501-4

Reference yield:

Phenylselenyl chloride (5707-04-0) + tert-butyl (S)-2-(((tert-butyldimethylsilyl)oxy)methyl)-5-oxopyrrolidin-1-carboxylate (81658-26-6) → (5S)-N-(tert-Butoxycarbonyl)-5-(((tert-butyldimethylsilyl)oxy)methyl)-3-(phenylseleno)pyrrolidin-2-one (293297-95-7)

Guidance literature:

With lithium diisopropyl amide; Yield given. Multistep reaction; 1.) THF, hexane, -78 deg C, 30 min, 2.) THF, 5 min;

DOI:10.1021/jo00013a018

Reference yield:

(S)-5-((tert-butyldimethylsilyloxy)methyl)pyrrolidin-2-one (106191-02-0) → (5S)-N-(tert-Butoxycarbonyl)-5-(((tert-butyldimethylsilyl)oxy)methyl)-3-(phenylseleno)pyrrolidin-2-one (293297-95-7)

Guidance literature:

Multi-step reaction with 2 steps

1.1: 99 percent / DMAP / acetonitrile / 0 - 20 °C

2.1: LiHMDS / tetrahydrofuran; hexane / 0.25 h / -78 °C

2.2: tetrahydrofuran; hexane / 1 h / -78 °C

With dmap; lithium hexamethyldisilazane; In tetrahydrofuran; hexane; acetonitrile;

DOI:10.1016/S0040-4020(01)00501-4

upstream raw materials:

Phenylselenyl chloride

tert-butyl (S)-2-(((tert-butyldimethylsilyl)oxy)methyl)-5-oxopyrrolidin-1-carboxylate

Phenylselenyl bromide

(S)-5-((tert-butyldimethylsilyloxy)methyl)pyrrolidin-2-one

Downstream raw materials:

(S)-tert-butyl 2-(((tert-butyldimethylsilyl)oxy)methyl)-5-oxo-2,5-dihydro-1H-pyrrole-1-carboxylate

(1S,2S,5R)-tert-butyl 3-aza-4-oxo-2-<(1,1,2,2-tetramethyl-1-silapropoxy)methyl>bicyclo<3.1.0>hexane-3-carboxylate

N-({(1S,2S,5R)-3-[(2-methyl-5-phenyl-1,3-thiazol-4-yl)carbonyl]-3-azabicyclo[3.1.0]hex-2-yl}methyl)-1,3-benzoxazol-2-amine

C₁₇H₁₉N₃OS