methyl (2S,4R)-1-allyloxycarbonyl-4-tert-butyldimethylsilyloxypyrrolidine-2-carboxylate

Base Information

• Chemical Name: methyl (2S,4R)-1-allyloxycarbonyl-4-tert-butyldimethylsilyloxypyrrolidine-2-carboxylate
• CAS No.: 156074-42-9
• Molecular Formula: C₁₆H₂₉NO₅Si
• Molecular Weight: 343.495

Synonyms:methyl (2S,4R)-1-allyloxycarbonyl-4-tert-butyldimethylsilyloxypyrrolidine-2-carboxylate

Chemical Property of methyl (2S,4R)-1-allyloxycarbonyl-4-tert-butyldimethylsilyloxypyrrolidine-2-carboxylate

Chemical Property:

Purity/Quality:

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Technology Process of methyl (2S,4R)-1-allyloxycarbonyl-4-tert-butyldimethylsilyloxypyrrolidine-2-carboxylate

There total 1 articles about methyl (2S,4R)-1-allyloxycarbonyl-4-tert-butyldimethylsilyloxypyrrolidine-2-carboxylate 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:

L-4-hydroxyproline methyl ester hydrochloride (40216-83-9) → methyl (2S,4R)-1-allyloxycarbonyl-4-tert-butyldimethylsilyloxypyrrolidine-2-carboxylate (156074-42-9)

Guidance literature:

Multi-step reaction with 2 steps

1: 88 percent / Et₃N / CH₂Cl₂ / 3 h / 20 °C

2: 83 percent / imidazole / dimethylformamide / 3 h / 20 °C

With 1H-imidazole; triethylamine; In dichloromethane; N,N-dimethyl-formamide;

DOI:10.1002/ardp.200300728

Reference yield:

1-bromomethyl-4-bromobenzene (589-15-1) + methyl (2S,4R)-1-allyloxycarbonyl-4-tert-butyldimethylsilyloxypyrrolidine-2-carboxylate (156074-42-9) → (2S,4R)-2-(4-bromo-benzyl)-4-(tert-butyl-dimethyl-silanyloxy)-pyrrolidine-1,2-dicarboxylic acid 1-allyl ester 2-methyl ester (934292-07-6) + (2R,4R)-2-(4-bromo-benzyl)-4-(tert-butyl-dimethyl-silanyloxy)-pyrrolidine-1,2-dicarboxylic acid 1-allyl ester 2-methyl ester (934292-08-7)

Guidance literature:

With potassium hexamethylsilazane; In tetrahydrofuran; at 20 - 40 ℃; for 0.333333h;

upstream raw materials:

L-4-hydroxyproline methyl ester hydrochloride

Downstream raw materials:

(2S,4R)-2-(4-bromo-benzyl)-4-(tert-butyl-dimethyl-silanyloxy)-pyrrolidine-1,2-dicarboxylic acid 1-allyl ester 2-methyl ester

(2R,4R)-2-(4-bromo-benzyl)-4-(tert-butyl-dimethyl-silanyloxy)-pyrrolidine-1,2-dicarboxylic acid 1-allyl ester 2-methyl ester

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