(S)-2-((Z)-2-tert-Butoxycarbonyl-2-cyano-1-hydroxy-vinyl)-pyrrolidine-1-carboxylic acid benzyl ester

Base Information

• Chemical Name: (S)-2-((Z)-2-tert-Butoxycarbonyl-2-cyano-1-hydroxy-vinyl)-pyrrolidine-1-carboxylic acid benzyl ester
• CAS No.: 866572-61-4
• Molecular Formula: C₂₀H₂₄N₂O₅
• Molecular Weight: 372.421

Synonyms:(S)-2-((Z)-2-tert-Butoxycarbonyl-2-cyano-1-hydroxy-vinyl)-pyrrolidine-1-carboxylic acid benzyl ester

Chemical Property of (S)-2-((Z)-2-tert-Butoxycarbonyl-2-cyano-1-hydroxy-vinyl)-pyrrolidine-1-carboxylic acid benzyl ester

Chemical Property:

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Technology Process of (S)-2-((Z)-2-tert-Butoxycarbonyl-2-cyano-1-hydroxy-vinyl)-pyrrolidine-1-carboxylic acid benzyl ester

There total 1 articles about (S)-2-((Z)-2-tert-Butoxycarbonyl-2-cyano-1-hydroxy-vinyl)-pyrrolidine-1-carboxylic acid 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:

cyanoacetic acid tert-butyl ester (1116-98-9) + Z-proline N-hydroxysuccinimide ester (3397-33-9) → (S)-2-((Z)-2-tert-Butoxycarbonyl-2-cyano-1-hydroxy-vinyl)-pyrrolidine-1-carboxylic acid benzyl ester (866572-61-4)

Guidance literature:

With sodium hydride; In benzene; at 25 ℃; for 3h;

DOI:10.1021/ol0518784

Reference yield:

(S)-2-((Z)-2-tert-Butoxycarbonyl-2-cyano-1-hydroxy-vinyl)-pyrrolidine-1-carboxylic acid benzyl ester (866572-61-4) → 2-(2-tert-butoxycarbonyl-2-cyano-1-hydroxy-ethyl)-pyrrolidine-1-carboxylic acid benzyl ester

Guidance literature:

With hydrogen; palladium on activated charcoal; In methanol; at 25 ℃; for 2h; under 760 Torr;

DOI:10.1021/jo061650+

Reference yield:

(S)-2-((Z)-2-tert-Butoxycarbonyl-2-cyano-1-hydroxy-vinyl)-pyrrolidine-1-carboxylic acid benzyl ester (866572-61-4) → 3-amino-5,6,7,7a-tetrahydro-1H-pyrrolizin-1-one

Guidance literature:

Multi-step reaction with 4 steps

1.1: hydrogen / palladium on carbon / methanol / 2 h / 25 °C / 760 Torr

2.1: 190 mg / 24 h / 25 °C

3.1: sodium hydride / tetrahydrofuran / 2 h

3.2: 39 percent / trifluoroacetic acid / CH₂Cl₂ / 15 h

4.1: 18 percent / sodium carbonate / methanol; H₂O / 6 h / 0 °C

With hydrogen; sodium hydride; sodium carbonate; palladium on activated charcoal; In tetrahydrofuran; methanol; water;

DOI:10.1021/jo061650+

upstream raw materials:

cyanoacetic acid tert-butyl ester

Z-proline N-hydroxysuccinimide ester

Downstream raw materials:

(7aS)-tert-butyl 3-amino-5,6,7,7a-tetrahydro-1-oxo-1H-pyrrolizine-2-carboxylate

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