2-tert-Butoxycarbonylmethyl-pyrrolidine-1,2-dicarboxylic acid 1-benzyl ester 2-methyl ester

Base Information

• Chemical Name: 2-tert-Butoxycarbonylmethyl-pyrrolidine-1,2-dicarboxylic acid 1-benzyl ester 2-methyl ester
• CAS No.: 195453-57-7
• Molecular Formula: C₂₀H₂₇NO₆
• Molecular Weight: 377.437

Synonyms:2-tert-Butoxycarbonylmethyl-pyrrolidine-1,2-dicarboxylic acid 1-benzyl ester 2-methyl ester

Chemical Property of 2-tert-Butoxycarbonylmethyl-pyrrolidine-1,2-dicarboxylic acid 1-benzyl ester 2-methyl ester

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Technology Process of 2-tert-Butoxycarbonylmethyl-pyrrolidine-1,2-dicarboxylic acid 1-benzyl ester 2-methyl ester

There total 2 articles about 2-tert-Butoxycarbonylmethyl-pyrrolidine-1,2-dicarboxylic acid 1-benzyl 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: 80.0%

bromoacetic acid tert-butyl ester (5292-43-3) + N-carbobenzyloxy-L-proline methyl ester (5211-23-4) → 2-tert-Butoxycarbonylmethyl-pyrrolidine-1,2-dicarboxylic acid 1-benzyl ester 2-methyl ester (195453-57-7)

Guidance literature:

With tetrahydrofuran; lithium diisopropyl amide; In tetrahydrofuran; hexane;

DOI:10.1002/hlca.19970800514

Reference yield:

N-Benzyloxycarbonyl-L-proline (1148-11-4) → 2-tert-Butoxycarbonylmethyl-pyrrolidine-1,2-dicarboxylic acid 1-benzyl ester 2-methyl ester (195453-57-7)

Guidance literature:

Multi-step reaction with 2 steps

1: 100 percent / thionyl chloride / rt., 1 h, then reflux, 2 h

2: 80 percent / LDA/THF complex / tetrahydrofuran; hexane

With tetrahydrofuran; thionyl chloride; lithium diisopropyl amide; In tetrahydrofuran; hexane;

DOI:10.1002/hlca.19970800514

Reference yield: 83.0%

2-tert-Butoxycarbonylmethyl-pyrrolidine-1,2-dicarboxylic acid 1-benzyl ester 2-methyl ester (195453-57-7) → 2-tert-Butoxycarbonylmethyl-pyrrolidine-1,2-dicarboxylic acid 1-benzyl ester (195453-61-3)

Guidance literature:

With lithium hydroxide; In methanol; water; for 15h;

DOI:10.1002/hlca.19970800514

upstream raw materials:

bromoacetic acid tert-butyl ester

N-carbobenzyloxy-L-proline methyl ester

N-Benzyloxycarbonyl-L-proline

Downstream raw materials:

2-tert-Butoxycarbonylmethyl-pyrrolidine-1,2-dicarboxylic acid 1-benzyl ester

[(2R,5aS,10aS)-5,10-Dioxo-2-(toluene-4-sulfonyloxy)-hexahydro-dipyrrolo[1,2-a;1',2'-d]pyrazin-5a-yl]-acetic acid tert-butyl ester

tert-butyl (2R)-1-[(benzyloxy)carbonyl]-2-{[(2S,4R)-4-hydroxy-2-(methoxycarbonyl)pyrrolidin-1-yl]carbonyl}pyrrolidine-2-acetate

tert-butyl (2S)-1-[(benzyloxy)carbonyl]-2-{[(2S,4R)-4-hydroxy-2-(methoxycarbonyl)pyrrolidin-1-yl]carbonyl}pyrrolidine-2-acetate

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