(5R)-5-(tert-butyldiphenylsilanyloxymethyl)-2-oxopyrrolidine-1,3-dicarboxylic acid 1-tert-butyl ester

Base Information

• Chemical Name: (5R)-5-(tert-butyldiphenylsilanyloxymethyl)-2-oxopyrrolidine-1,3-dicarboxylic acid 1-tert-butyl ester
• CAS No.: 449143-41-3
• Molecular Formula: C₂₇H₃₅NO₆Si
• Molecular Weight: 497.663
• Mol file: 449143-41-3.mol

Synonyms:(5R)-5-(tert-butyldiphenylsilanyloxymethyl)-2-oxopyrrolidine-1,3-dicarboxylic acid 1-tert-butyl ester

Chemical Property of (5R)-5-(tert-butyldiphenylsilanyloxymethyl)-2-oxopyrrolidine-1,3-dicarboxylic acid 1-tert-butyl ester

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (5R)-5-(tert-butyldiphenylsilanyloxymethyl)-2-oxopyrrolidine-1,3-dicarboxylic acid 1-tert-butyl ester

There total 9 articles about (5R)-5-(tert-butyldiphenylsilanyloxymethyl)-2-oxopyrrolidine-1,3-dicarboxylic acid 1-tert-butyl 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: 90.0%

(5R)-5-(tert-butyldiphenylsilanyloxymethyl)-2-oxopyrrolidine-1,3-dicarboxylic acid 3-benzyl ester 1 tert-butyl ester (449143-53-7) → (5R)-5-(tert-butyldiphenylsilanyloxymethyl)-2-oxopyrrolidine-1,3-dicarboxylic acid 1-tert-butyl ester (449143-41-3)

Guidance literature:

With hydrogen; palladium on activated charcoal; In ethyl acetate; for 8h; Ambient temperature;

DOI:10.1016/S0040-4039(00)75792-3

Reference yield:

(R)-5-hydroxymethylpyrrolidin-2-one (66673-40-3) → (5R)-5-(tert-butyldiphenylsilanyloxymethyl)-2-oxopyrrolidine-1,3-dicarboxylic acid 1-tert-butyl ester (449143-41-3)

Guidance literature:

Multi-step reaction with 4 steps

1.1: 95 percent / imidazole / dimethylformamide / 5 h / 20 °C

2.1: 93 percent / DMAP; triethylamine / CH₂Cl₂ / 0 - 20 °C

3.1: HMDS; n-BuLi / tetrahydrofuran; hexane / 1 h / -78 °C

3.2: 99 percent / tetrahydrofuran; hexane / 0.75 h / -78 - 20 °C

4.1: 90 percent / H₂ / Pd/C / ethyl acetate / 22 h

With 1H-imidazole; dmap; n-butyllithium; hydrogen; triethylamine; 1,1,1,3,3,3-hexamethyl-disilazane; palladium on activated charcoal; In tetrahydrofuran; hexane; dichloromethane; ethyl acetate; N,N-dimethyl-formamide;

DOI:10.1021/ja0202964

Reference yield:

(R)-5-(tert-butyl-diphenyl-silanyloxymethyl)-pyrrolidin-2-one (138629-44-4) → (5R)-5-(tert-butyldiphenylsilanyloxymethyl)-2-oxopyrrolidine-1,3-dicarboxylic acid 1-tert-butyl ester (449143-41-3)

Guidance literature:

Multi-step reaction with 3 steps

1.1: 93 percent / DMAP; triethylamine / CH₂Cl₂ / 0 - 20 °C

2.1: HMDS; n-BuLi / tetrahydrofuran; hexane / 1 h / -78 °C

2.2: 99 percent / tetrahydrofuran; hexane / 0.75 h / -78 - 20 °C

3.1: 90 percent / H₂ / Pd/C / ethyl acetate / 22 h

With dmap; n-butyllithium; hydrogen; triethylamine; 1,1,1,3,3,3-hexamethyl-disilazane; palladium on activated charcoal; In tetrahydrofuran; hexane; dichloromethane; ethyl acetate;

DOI:10.1021/ja0202964

upstream raw materials:

(5R)-5-(tert-butyldiphenylsilanyloxymethyl)-2-oxopyrrolidine-1,3-dicarboxylic acid 3-benzyl ester 1 tert-butyl ester

carbon dioxide

(5R)-5-(tert-butyldiphenylsilanyloxymethyl)-2-oxopyrrolidine-1-carboxylic acid tert-butyl ester

di-tert-butyl dicarbonate

Downstream raw materials:

1-tert-butyl 8-methyl (2R,3aS,7aR,10aS)-5-benzyl-2-[(tert-butyldiphenylsilanyloxy)methyl]-4-oxo-2,3,5,6,7,7a,10,10a-octahydropyrrolo[2.3-i]isoquinoline-1,8(4H)-dicarboxylate

methyl (2R,3aS,7aR,10aS)-5-benzyl-2-[(tert-butyldiphenylsilanyloxy)methyl]-1-(hex-5-enoyl)-4-oxo-1,2,3,4,5,6,7,7a,10,10a-decahydropyrrolo[2.3-i]isoquinoline-8-carboxylate

2(R)-4-{N-benzyl-N-[4'-methoxycarbonylhexa-3'(E),5'-dien-1'-yl]carbamoyl}-2-(tert-butyldiphenylsilanyloxymethyl)-2,3-dihydropyrrole-1-carboxylic acid tert-butyl ester

methyl (2R,3aS,7aR,10aS)-5-benzyl-2-[(tert-butyl-diphenylsilanyloxy)methyl]-4-oxo-1,2,3,4,5,6,7,7a,10,10a-decahydropyrrolo[2.3-i]isoquinoline-8-carboxylate