(2S,3R)-2-(tert-butyl-dimethyl-silanyloxymethyl)-3-(4-methoxy-phenyl)-5-oxo-pyrrolidine-1-carboxylic acid tert-butyl ester

Base Information

• Chemical Name: (2S,3R)-2-(tert-butyl-dimethyl-silanyloxymethyl)-3-(4-methoxy-phenyl)-5-oxo-pyrrolidine-1-carboxylic acid tert-butyl ester
• CAS No.: 855517-77-0
• Molecular Formula: C₂₃H₃₇NO₅Si
• Molecular Weight: 435.636
• Mol file: 855517-77-0.mol

Synonyms:(2S,3R)-2-(tert-butyl-dimethyl-silanyloxymethyl)-3-(4-methoxy-phenyl)-5-oxo-pyrrolidine-1-carboxylic acid tert-butyl ester

Chemical Property of (2S,3R)-2-(tert-butyl-dimethyl-silanyloxymethyl)-3-(4-methoxy-phenyl)-5-oxo-pyrrolidine-1-carboxylic acid tert-butyl ester

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (2S,3R)-2-(tert-butyl-dimethyl-silanyloxymethyl)-3-(4-methoxy-phenyl)-5-oxo-pyrrolidine-1-carboxylic acid tert-butyl ester

There total 1 articles about (2S,3R)-2-(tert-butyl-dimethyl-silanyloxymethyl)-3-(4-methoxy-phenyl)-5-oxo-pyrrolidine-1-carboxylic acid 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%

(S)-tert-butyl 2-(((tert-butyldimethylsilyl)oxy)methyl)-5-oxo-2,5-dihydro-1H-pyrrole-1-carboxylate (81658-27-7) + 4-methoxyphenyl magnesium bromide (13139-86-1) → (2S,3R)-2-(tert-butyl-dimethyl-silanyloxymethyl)-3-(4-methoxy-phenyl)-5-oxo-pyrrolidine-1-carboxylic acid tert-butyl ester (855517-77-0)

Guidance literature:

4-methoxyphenyl magnesium bromide; With copper(I) bromide dimethylsulfide complex; In tetrahydrofuran; for 0.5h; cooling;

(S)-tert-butyl 2-(((tert-butyldimethylsilyl)oxy)methyl)-5-oxo-2,5-dihydro-1H-pyrrole-1-carboxylate; With chloro-trimethyl-silane; In tetrahydrofuran; at -78 - 20 ℃;

DOI:10.1016/j.tet.2005.03.042

Reference yield:

(2S,3R)-2-(tert-butyl-dimethyl-silanyloxymethyl)-3-(4-methoxy-phenyl)-5-oxo-pyrrolidine-1-carboxylic acid tert-butyl ester (855517-77-0) → (2S,3R,4R)-4-carboxymethyl-3-(4-methoxyphenyl)-5-oxo-pyrrolidine-1,2-dicarboxylic acid 1-tert-butyl ester 2-methyl ester (855517-81-6)

Guidance literature:

Multi-step reaction with 5 steps

1.1: lithium hexamethyldisilazide / tetrahydrofuran / 0.5 h / -78 °C

1.2: 1.50 g / tetrahydrofuran / -78 - 20 °C

2.1: lithium hexamethyldisilazide / tetrahydrofuran / 0.67 h / -78 °C

2.2: 73 percent / acetic acid / tetrahydrofuran / cooling

3.1: Jones reagent / acetone / 0 - 20 °C

4.1: 664 mg / diethyl ether / 0.17 h / 20 °C

5.1: 68 percent / hydrogen / Pd/C / ethyl acetate / 3 h / 20 °C / 760 Torr

With jones reagent; hydrogen; lithium hexamethyldisilazane; palladium on activated charcoal; In tetrahydrofuran; diethyl ether; ethyl acetate; acetone;

DOI:10.1016/j.tet.2005.03.042

Reference yield:

(2S,3R)-2-(tert-butyl-dimethyl-silanyloxymethyl)-3-(4-methoxy-phenyl)-5-oxo-pyrrolidine-1-carboxylic acid tert-butyl ester (855517-77-0) + Benzyl bromoacetate (5437-45-6) → (3S,4R,5S)-3-benzyloxycarbonylmethyl-5-(tert-butyldimethyl-silanyloxymethyl)-4-(4-methoxy-phenyl)-2-oxo-pyrrolidine-1-carboxylic acid tert-butyl ester (855517-78-1) + (3R,4R,5S)-3-benzyloxycarbonylmethyl-5-(tert-butyldimethyl-silanyloxymethyl)-4-(4-methoxy-phenyl)-2-oxo-pyrrolidine-1-carboxylic acid tert-butyl ester (855517-79-2)

Guidance literature:

(2S,3R)-2-(tert-butyl-dimethyl-silanyloxymethyl)-3-(4-methoxy-phenyl)-5-oxo-pyrrolidine-1-carboxylic acid tert-butyl ester; With lithium hexamethyldisilazane; In tetrahydrofuran; at -78 ℃; for 0.5h;

Benzyl bromoacetate; In tetrahydrofuran; at -78 - 20 ℃;

DOI:10.1016/j.tet.2005.03.042

upstream raw materials:

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

4-methoxyphenyl magnesium bromide

Downstream raw materials:

(3S,4R,5S)-3-benzyloxycarbonylmethyl-5-(tert-butyldimethyl-silanyloxymethyl)-4-(4-methoxy-phenyl)-2-oxo-pyrrolidine-1-carboxylic acid tert-butyl ester

(3R,4R,5S)-3-benzyloxycarbonylmethyl-5-(tert-butyldimethyl-silanyloxymethyl)-4-(4-methoxy-phenyl)-2-oxo-pyrrolidine-1-carboxylic acid tert-butyl ester

(2S,3R,4R)-4-carboxymethyl-3-(4-methoxyphenyl)-5-oxo-pyrrolidine-1,2-dicarboxylic acid 1-tert-butyl ester 2-methyl ester

(2S,3R,4R)-4-benzyloxycarbonylmethyl-3-(4-methoxy-phenyl)-5-oxo-pyrrolidine-1,2-dicarboxylic acid 1-tert-butyl ester 2-methyl ester