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

Base Information

Chemical Name:(2S,3R,4R)-4-carboxymethyl-3-(4-methoxyphenyl)-5-oxo-pyrrolidine-1,2-dicarboxylic acid 1-tert-butyl ester 2-methyl ester
CAS No.:855517-81-6
Molecular Formula:C₂₀H₂₅NO₈
Molecular Weight:407.42
Hs Code.:

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

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

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

There total 7 articles about (2S,3R,4R)-4-carboxymethyl-3-(4-methoxyphenyl)-5-oxo-pyrrolidine-1,2-dicarboxylic acid 1-tert-butyl ester 2-methyl 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: 68.0%

: 855517-80-5
(2S,3R,4R)-4-benzyloxycarbonylmethyl-3-(4-methoxy-phenyl)-5-oxo-pyrrolidine-1,2-dicarboxylic acid 1-tert-butyl ester 2-methyl ester

: 855517-81-6
(2S,3R,4R)-4-carboxymethyl-3-(4-methoxyphenyl)-5-oxo-pyrrolidine-1,2-dicarboxylic acid 1-tert-butyl ester 2-methyl ester

Guidance literature:: With hydrogen; palladium on activated charcoal; In ethyl acetate; at 20 ℃; for 3h; under 760 Torr;
DOI:10.1016/j.tet.2005.03.042

Reference yield:

: 855517-77-0
(2S,3R)-2-(tert-butyl-dimethyl-silanyloxymethyl)-3-(4-methoxy-phenyl)-5-oxo-pyrrolidine-1-carboxylic acid tert-butyl ester

: 855517-81-6
(2S,3R,4R)-4-carboxymethyl-3-(4-methoxyphenyl)-5-oxo-pyrrolidine-1,2-dicarboxylic acid 1-tert-butyl ester 2-methyl ester

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:

: 81658-27-7
(S)-tert-butyl 2-(((tert-butyldimethylsilyl)oxy)methyl)-5-oxo-2,5-dihydro-1H-pyrrole-1-carboxylate

: 855517-81-6
(2S,3R,4R)-4-carboxymethyl-3-(4-methoxyphenyl)-5-oxo-pyrrolidine-1,2-dicarboxylic acid 1-tert-butyl ester 2-methyl ester

Guidance literature:: Multi-step reaction with 6 steps

1.1: CuBr*Me₂S / tetrahydrofuran / 0.5 h / cooling

1.2: 90 percent / trimethylsilyl chloride / tetrahydrofuran / -78 - 20 °C

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

2.2: 1.50 g / tetrahydrofuran / -78 - 20 °C

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

3.2: 73 percent / acetic acid / tetrahydrofuran / cooling

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

5.1: 664 mg / diethyl ether / 0.17 h / 20 °C

6.1: 68 percent / hydrogen / Pd/C / ethyl acetate / 3 h / 20 °C / 760 Torr

With jones reagent; copper(I) bromide dimethylsulfide complex; hydrogen; lithium hexamethyldisilazane; palladium on activated charcoal; In tetrahydrofuran; diethyl ether; ethyl acetate; acetone; 1.2: Michael addition;
DOI:10.1016/j.tet.2005.03.042