(S)-4-methylene-pyrrolidine-1,2-dicarboxylic acid 2-benzyl ester 1-tert-butyl ester

Base Information

• Chemical Name: (S)-4-methylene-pyrrolidine-1,2-dicarboxylic acid 2-benzyl ester 1-tert-butyl ester
• CAS No.: 159830-01-0
• Molecular Formula: C₁₈H₂₃NO₄
• Molecular Weight: 317.385
• Mol file: 159830-01-0.mol

Synonyms:(S)-4-methylene-pyrrolidine-1,2-dicarboxylic acid 2-benzyl ester 1-tert-butyl ester

Chemical Property of (S)-4-methylene-pyrrolidine-1,2-dicarboxylic acid 2-benzyl ester 1-tert-butyl ester

Chemical Property:

Purity/Quality:

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Technology Process of (S)-4-methylene-pyrrolidine-1,2-dicarboxylic acid 2-benzyl ester 1-tert-butyl ester

There total 9 articles about (S)-4-methylene-pyrrolidine-1,2-dicarboxylic acid 2-benzyl ester 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: 73.0%

benzyl bromide (100-39-0) + (S)-1-(tert-butoxycarbonyl)-4-methylenepyrrolidine-2-carboxylic acid (84348-38-9,1427175-11-8) → (S)-4-methylene-pyrrolidine-1,2-dicarboxylic acid 2-benzyl ester 1-tert-butyl ester (159830-01-0)

Guidance literature:

With caesium carbonate; In N,N-dimethyl-formamide; at 0 - 20 ℃;

Reference yield: 60.0%

C20H30N2O5 → N,N-dimethylhydroxylamine (5725-96-2) + (S)-4-methylene-pyrrolidine-1,2-dicarboxylic acid 2-benzyl ester 1-tert-butyl ester (159830-01-0) + (S)-4-Dimethylaminomethyl-pyrrolidine-1,2-dicarboxylic acid 2-benzyl ester 1-tert-butyl ester

Guidance literature:

In tetrahydrofuran; toluene; at 85 ℃;

DOI:10.1016/S0040-4039(00)73465-4

Reference yield:

di-tert-butyl dicarbonate (24424-99-5) → (S)-4-methylene-pyrrolidine-1,2-dicarboxylic acid 2-benzyl ester 1-tert-butyl ester (159830-01-0)

Guidance literature:

Multi-step reaction with 3 steps

1: triethylamine; dmap / dichloromethane / 48 h / 20 °C / Inert atmosphere

2: potassium hydroxide / methanol; water; tetrahydrofuran / 32 h / 20 °C

3: caesium carbonate / N,N-dimethyl-formamide / 20 °C / Inert atmosphere

With dmap; caesium carbonate; triethylamine; potassium hydroxide; In tetrahydrofuran; methanol; dichloromethane; water; N,N-dimethyl-formamide;

DOI:10.3390/molecules25235644

upstream raw materials:

benzyl (2S)-N-tert-butoxycarbonyl-5-oxoprolinate

benzyl bromide

(S)-1-(tert-butoxycarbonyl)-4-methylenepyrrolidine-2-carboxylic acid

di-tert-butyl dicarbonate