benzyl (-)-(3R,4S)-3-(benzyloxycarbonylamino)-4-hydroxypyrrolidine-1-carboxylate

Base Information

• Chemical Name: benzyl (-)-(3R,4S)-3-(benzyloxycarbonylamino)-4-hydroxypyrrolidine-1-carboxylate
• CAS No.: 1262306-33-1
• Molecular Formula: C₂₀H₂₂N₂O₅
• Molecular Weight: 370.405
• Mol file: 1262306-33-1.mol

Synonyms:benzyl (-)-(3R,4S)-3-(benzyloxycarbonylamino)-4-hydroxypyrrolidine-1-carboxylate

Chemical Property of benzyl (-)-(3R,4S)-3-(benzyloxycarbonylamino)-4-hydroxypyrrolidine-1-carboxylate

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of benzyl (-)-(3R,4S)-3-(benzyloxycarbonylamino)-4-hydroxypyrrolidine-1-carboxylate

There total 3 articles about benzyl (-)-(3R,4S)-3-(benzyloxycarbonylamino)-4-hydroxypyrrolidine-1-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:

1-carboxybenzyl-3-pyrrolidine (31970-04-4) + benzyloxycarbonylamino-4-chlorobenzoate (1262306-22-8) → benzyl (+)-(3S,4R)-3-(benzyloxycarbonylamino)-4-hydroxypyrrolidine-1-carboxylate (1262306-34-2) + benzyl (-)-(3R,4S)-3-(benzyloxycarbonylamino)-4-hydroxypyrrolidine-1-carboxylate (1262306-33-1)

Guidance literature:

benzyloxycarbonylamino-4-chlorobenzoate; With osmium(VIII) oxide; hydroquinidein 1,4-phthalazinediyl diether; In acetonitrile; at 20 ℃; for 0.166667h;

1-carboxybenzyl-3-pyrrolidine; In water; acetonitrile; at 20 ℃; for 3h; optical yield given as %ee; enantioselective reaction;

DOI:10.1021/jo1018816

Reference yield:

benzyl chloroformate (501-53-1,94274-21-2) → benzyl (+)-(3S,4R)-3-(benzyloxycarbonylamino)-4-hydroxypyrrolidine-1-carboxylate (1262306-34-2) + benzyl (-)-(3R,4S)-3-(benzyloxycarbonylamino)-4-hydroxypyrrolidine-1-carboxylate (1262306-33-1)

Guidance literature:

Multi-step reaction with 3 steps

1.1: hydroxylamine hydrochloride; sodium carbonate / water / 20 - 45 °C

2.1: triethylamine / diethyl ether / 0 - 20 °C

3.1: osmium(VIII) oxide; 1,4-bis(9-O-dihydroquinidine)phthalazine / acetonitrile / 0.17 h / 20 °C

3.2: 3 h / 20 °C

With osmium(VIII) oxide; hydroxylamine hydrochloride; sodium carbonate; 1,4-bis(9-O-dihydroquinidine)phthalazine; triethylamine; In diethyl ether; water; acetonitrile;

DOI:10.1021/jo1018816

Reference yield:

Benzyl N-hydroxycarbamate (3426-71-9) → benzyl (+)-(3S,4R)-3-(benzyloxycarbonylamino)-4-hydroxypyrrolidine-1-carboxylate (1262306-34-2) + benzyl (-)-(3R,4S)-3-(benzyloxycarbonylamino)-4-hydroxypyrrolidine-1-carboxylate (1262306-33-1)

Guidance literature:

Multi-step reaction with 2 steps

1.1: triethylamine / diethyl ether / 0 - 20 °C

2.1: osmium(VIII) oxide; 1,4-bis(9-O-dihydroquinidine)phthalazine / acetonitrile / 0.17 h / 20 °C

2.2: 3 h / 20 °C

With osmium(VIII) oxide; 1,4-bis(9-O-dihydroquinidine)phthalazine; triethylamine; In diethyl ether; acetonitrile;

DOI:10.1021/jo1018816

upstream raw materials:

Benzyl N-hydroxycarbamate

1-carboxybenzyl-3-pyrrolidine

benzyloxycarbonylamino-4-chlorobenzoate

benzyl chloroformate