4(S)-Benzyloxy-N-tert-butyl-1-(tert-butyloxycarbonyl) pyrrolidine-2(S)-carboxamide

Base Information

• Chemical Name: 4(S)-Benzyloxy-N-tert-butyl-1-(tert-butyloxycarbonyl) pyrrolidine-2(S)-carboxamide
• CAS No.: 148983-10-2
• Molecular Formula: C₂₁H₃₂N₂O₄
• Molecular Weight: 376.496
• Mol file: 148983-10-2.mol

Synonyms:4(S)-Benzyloxy-N-tert-butyl-1-(tert-butyloxycarbonyl) pyrrolidine-2(S)-carboxamide

Chemical Property of 4(S)-Benzyloxy-N-tert-butyl-1-(tert-butyloxycarbonyl) pyrrolidine-2(S)-carboxamide

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of 4(S)-Benzyloxy-N-tert-butyl-1-(tert-butyloxycarbonyl) pyrrolidine-2(S)-carboxamide

There total 3 articles about 4(S)-Benzyloxy-N-tert-butyl-1-(tert-butyloxycarbonyl) pyrrolidine-2(S)-carboxamide 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: 55.0%

benzyl bromide (100-39-0) + (2S,4S)-2-tert-Butylcarbamoyl-4-hydroxy-pyrrolidine-1-carboxylic acid tert-butyl ester (153290-81-4) → 4(S)-Benzyloxy-N-tert-butyl-1-(tert-butyloxycarbonyl) pyrrolidine-2(S)-carboxamide (148983-10-2)

Guidance literature:

With sodium hydride; In N,N-dimethyl-formamide;

DOI:10.1021/jm00048a007

Reference yield:

N-tert-butoxycarbonyl-L-cis-4-hydroxyproline (87691-27-8,946610-68-0) → 4(S)-Benzyloxy-N-tert-butyl-1-(tert-butyloxycarbonyl) pyrrolidine-2(S)-carboxamide (148983-10-2)

Guidance literature:

Multi-step reaction with 2 steps

1: DIPEA, TBTU / dimethylformamide / Ambient temperature

2: 55 percent / NaH / dimethylformamide

With sodium hydride; O-(benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium tetrafluoroborate; N-ethyl-N,N-diisopropylamine; In N,N-dimethyl-formamide;

DOI:10.1021/jm00048a007

Reference yield:

(2S,4S)-4-(benzyloxy)-1-(tert-butoxycarbonyl)pyrrolidine-2-carboxylic acid (40350-83-2,54631-81-1,54631-82-2) + tert-butylamine (75-64-9) → 4(S)-Benzyloxy-N-tert-butyl-1-(tert-butyloxycarbonyl) pyrrolidine-2(S)-carboxamide (148983-10-2)

Guidance literature:

With O-(benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium tetrafluoroborate; N-ethyl-N,N-diisopropylamine; In N,N-dimethyl-formamide; Ambient temperature;

DOI:10.1021/jm00048a007

upstream raw materials:

benzyl bromide

(2S,4S)-2-tert-Butylcarbamoyl-4-hydroxy-pyrrolidine-1-carboxylic acid tert-butyl ester

(2S,4S)-4-(benzyloxy)-1-(tert-butoxycarbonyl)pyrrolidine-2-carboxylic acid

tert-butylamine