methyl (2S,4E)-1-(benzyloxycarbonyl)-4-(2-tert-butoxy-2-oxoethylidene)-2-pyrrolidinecarboxylate

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Chemical Name:methyl (2S,4E)-1-(benzyloxycarbonyl)-4-(2-tert-butoxy-2-oxoethylidene)-2-pyrrolidinecarboxylate
CAS No.:117653-36-8
Molecular Formula:C₂₀H₂₅NO₆
Molecular Weight:375.422
Hs Code.:

Synonyms:methyl (2S,4E)-1-(benzyloxycarbonyl)-4-(2-tert-butoxy-2-oxoethylidene)-2-pyrrolidinecarboxylate

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Chemical Property of methyl (2S,4E)-1-(benzyloxycarbonyl)-4-(2-tert-butoxy-2-oxoethylidene)-2-pyrrolidinecarboxylate

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Technology Process of methyl (2S,4E)-1-(benzyloxycarbonyl)-4-(2-tert-butoxy-2-oxoethylidene)-2-pyrrolidinecarboxylate

There total 3 articles about methyl (2S,4E)-1-(benzyloxycarbonyl)-4-(2-tert-butoxy-2-oxoethylidene)-2-pyrrolidinecarboxylate 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: 48.0%

: 41108-81-0
tert-butyl (trimethylsilyl)acetate

: 16217-15-5
1-benzyloxycarbonyl-4-oxo-L-proline methyl ester

: 117653-35-7,117653-36-8
2-methyl-1-(phenylmethyl) 4-<2-(1,1-dimethylethoxy)-2-oxoethylidene>-1,2-pyrrolidinedicarboxylate

Guidance literature:: With n-butyllithium; diisopropylamine; In tetrahydrofuran; at -78 ℃; for 2.5h;
DOI:10.1021/jo00262a026

Reference yield: 39.0%

: 41108-81-0
tert-butyl (trimethylsilyl)acetate

: 16217-15-5
1-benzyloxycarbonyl-4-oxo-L-proline methyl ester

: 117653-36-8
methyl (2S,4E)-1-(benzyloxycarbonyl)-4-(2-tert-butoxy-2-oxoethylidene)-2-pyrrolidinecarboxylate

Guidance literature:: tert-butyl (trimethylsilyl)acetate; With lithium diisopropyl amide; In tetrahydrofuran; hexane; at -78 ℃; for 0.25h;

1-benzyloxycarbonyl-4-oxo-L-proline methyl ester; In tetrahydrofuran; hexane; at -78 ℃; for 3h; Further stages.;
DOI:10.1016/j.bmc.2007.01.041

Reference yield:

: 64187-48-0
methyl (2S,4R)-1-benzyloxycarbonyl-4-hydroxypyrrolidine-2-carboxylate

: 117653-36-8
methyl (2S,4E)-1-(benzyloxycarbonyl)-4-(2-tert-butoxy-2-oxoethylidene)-2-pyrrolidinecarboxylate

Guidance literature:: Multi-step reaction with 2 steps

1.1: 58 percent / triethylamine; DMSO; pyridine-sulfur trioxide / ethyl acetate / 88 h / 20 °C

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

2.2: 39 percent / tetrahydrofuran; hexane / 3 h / -78 °C

With sulfur trioxide pyridine complex; dimethyl sulfoxide; triethylamine; lithium diisopropyl amide; In tetrahydrofuran; hexane; ethyl acetate; 2.2: Peterson reaction;
DOI:10.1016/j.bmc.2007.01.041