(2S,5R)-2-(tert-Butyl-dimethyl-silanyloxymethyl)-5-hydroxymethyl-pyrrolidine-1-carboxylic acid benzyl ester

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Chemical Name:(2S,5R)-2-(tert-Butyl-dimethyl-silanyloxymethyl)-5-hydroxymethyl-pyrrolidine-1-carboxylic acid benzyl ester
CAS No.:172885-66-4
Molecular Formula:C₂₀H₃₃NO₄Si
Molecular Weight:379.572
Hs Code.:

Synonyms:(2S,5R)-2-(tert-Butyl-dimethyl-silanyloxymethyl)-5-hydroxymethyl-pyrrolidine-1-carboxylic acid benzyl ester

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Chemical Property of (2S,5R)-2-(tert-Butyl-dimethyl-silanyloxymethyl)-5-hydroxymethyl-pyrrolidine-1-carboxylic acid benzyl ester

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Technology Process of (2S,5R)-2-(tert-Butyl-dimethyl-silanyloxymethyl)-5-hydroxymethyl-pyrrolidine-1-carboxylic acid benzyl ester

There total 5 articles about (2S,5R)-2-(tert-Butyl-dimethyl-silanyloxymethyl)-5-hydroxymethyl-pyrrolidine-1-carboxylic acid benzyl ester 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: 93.0%

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

: 173006-75-2
[(2R,5S)-5-(tert-Butyl-dimethyl-silanyloxymethyl)-pyrrolidin-2-yl]-methanol

: 172885-66-4
(2S,5R)-2-(tert-Butyl-dimethyl-silanyloxymethyl)-5-hydroxymethyl-pyrrolidine-1-carboxylic acid benzyl ester

Guidance literature:: With triethylamine; In dichloromethane; at 0 ℃; for 18h;
DOI:10.1021/jo951469t

Reference yield:

: 102572-59-8
(2S,5R)-N-benzyl-5-methoxycarbonylproline

: 172885-66-4
(2S,5R)-2-(tert-Butyl-dimethyl-silanyloxymethyl)-5-hydroxymethyl-pyrrolidine-1-carboxylic acid benzyl ester

Guidance literature:: Multi-step reaction with 5 steps

1: 1.) Et₃N, ClCO₂Et, 2.) NaBH₄ / 1.) THF, 0 deg C, 3 h, 2.) H₂O, 0 deg C, 1 h

2: 2.40 g / imidazole / dimethylformamide / 24 h / 25 °C

3: DIBALH / toluene; hexane / 0.83 h / 25 °C

4: 100 percent / H₂ / Pd(OH)2/C / ethanol / 18 h / 25 °C / 760 Torr

5: 93 percent / Et₃N / CH₂Cl₂ / 18 h / 0 °C

With 1H-imidazole; sodium tetrahydroborate; hydrogen; chloroformic acid ethyl ester; diisobutylaluminium hydride; triethylamine; palladium dihydroxide; In ethanol; hexane; dichloromethane; N,N-dimethyl-formamide; toluene;
DOI:10.1021/jo951469t

Reference yield:

: 113304-86-2
(2R,5S)-1-Benzyl-5-hydroxymethyl-pyrrolidine-2-carboxylic acid methyl ester

: 172885-66-4
(2S,5R)-2-(tert-Butyl-dimethyl-silanyloxymethyl)-5-hydroxymethyl-pyrrolidine-1-carboxylic acid benzyl ester

Guidance literature:: Multi-step reaction with 4 steps

1: 2.40 g / imidazole / dimethylformamide / 24 h / 25 °C

2: DIBALH / toluene; hexane / 0.83 h / 25 °C

3: 100 percent / H₂ / Pd(OH)2/C / ethanol / 18 h / 25 °C / 760 Torr

4: 93 percent / Et₃N / CH₂Cl₂ / 18 h / 0 °C

With 1H-imidazole; hydrogen; diisobutylaluminium hydride; triethylamine; palladium dihydroxide; In ethanol; hexane; dichloromethane; N,N-dimethyl-formamide; toluene;
DOI:10.1021/jo951469t