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

Base Information

• Chemical Name: 2-tert-Butoxycarbonylmethyl-pyrrolidine-1,2-dicarboxylic acid 1-benzyl ester
• CAS No.: 195453-61-3
• Molecular Formula: C₁₉H₂₅NO₆
• Molecular Weight: 363.411

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

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

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

There total 3 articles about 2-tert-Butoxycarbonylmethyl-pyrrolidine-1,2-dicarboxylic acid 1-benzyl 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: 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

Reference yield:

N-carbobenzyloxy-L-proline methyl ester (5211-23-4) → 2-tert-Butoxycarbonylmethyl-pyrrolidine-1,2-dicarboxylic acid 1-benzyl ester (195453-61-3)

Guidance literature:

Multi-step reaction with 2 steps

1: 80 percent / LDA/THF complex / tetrahydrofuran; hexane

2: 83 percent / LiOH*H₂O / methanol; H₂O / 15 h

With tetrahydrofuran; lithium hydroxide; lithium diisopropyl amide; In tetrahydrofuran; methanol; hexane; water;

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 (195453-61-3)

Guidance literature:

Multi-step reaction with 3 steps

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

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

3: 83 percent / LiOH*H₂O / methanol; H₂O / 15 h

With tetrahydrofuran; lithium hydroxide; thionyl chloride; lithium diisopropyl amide; In tetrahydrofuran; methanol; hexane; water;

DOI:10.1002/hlca.19970800514

upstream raw materials:

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

N-carbobenzyloxy-L-proline methyl ester

N-Benzyloxycarbonyl-L-proline

Downstream raw materials:

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

[(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

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