(3S,4S)-1-benzyl-3-(tert-butyldimethylsilyl)oxy-4-hydroxypyrrolidine

Base Information

• Chemical Name: (3S,4S)-1-benzyl-3-(tert-butyldimethylsilyl)oxy-4-hydroxypyrrolidine
• CAS No.: 201601-50-5
• Molecular Formula: C₁₇H₂₉NO₂Si
• Molecular Weight: 307.508
• Mol file: 201601-50-5.mol

Synonyms:(3S,4S)-1-benzyl-3-(tert-butyldimethylsilyl)oxy-4-hydroxypyrrolidine

Chemical Property of (3S,4S)-1-benzyl-3-(tert-butyldimethylsilyl)oxy-4-hydroxypyrrolidine

Chemical Property:

Purity/Quality:

97% ^*data from raw suppliers

(3S,4S)-1-benzyl-4-[(tert-butyldimethylsilyl)oxy]pyrrolidin-3-ol 97% ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (3S,4S)-1-benzyl-3-(tert-butyldimethylsilyl)oxy-4-hydroxypyrrolidine

There total 6 articles about (3S,4S)-1-benzyl-3-(tert-butyldimethylsilyl)oxy-4-hydroxypyrrolidine 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%

(3S,4S)-(+)-1-benzyl-3,4-pyrrolidinediol (90365-74-5,330152-66-4) + tert-butyldimethylsilyl chloride (18162-48-6) → (3S,4S)-1-benzyl-3-(tert-butyldimethylsilyl)oxy-4-hydroxypyrrolidine (201601-50-5)

Guidance literature:

(3S,4S)-(+)-1-benzyl-3,4-pyrrolidinediol; With sodium hydride; In tetrahydrofuran; for 0.25h; Inert atmosphere; Cooling with ice;

tert-butyldimethylsilyl chloride; In tetrahydrofuran; at 20 ℃; for 12h; Inert atmosphere; Cooling with ice;

DOI:10.1002/ejoc.202001581

Reference yield: 21.0%

(3S,4S)-(+)-1-benzyl-3,4-pyrrolidinediol (90365-74-5,330152-66-4) + tert-butyldimethylsilyl chloride (18162-48-6) → (3S,4S)-1-benzyl-3,4-bis{[(tert-butyl)dimethylsilyl]oxy}pyrrolidine (138228-45-2) + (3S,4S)-1-benzyl-3-(tert-butyldimethylsilyl)oxy-4-hydroxypyrrolidine (201601-50-5)

Guidance literature:

With 1H-imidazole; In N,N-dimethyl-formamide; Yield given; 1.) 0 deg C, 1 h, 2.) r.t., 12 h;

DOI:10.1039/a703583g

Reference yield:

(3R,4R)-1-Benzyl-3-(tert-butyl-dimethyl-silanyloxy)-4-hydroxy-pyrrolidine-2,5-dione → (3S,4S)-1-benzyl-3-(tert-butyldimethylsilyl)oxy-4-hydroxypyrrolidine (201601-50-5)

Guidance literature:

With borane-THF; In tetrahydrofuran; at 20 - 70 ℃;

DOI:10.1016/S0957-4166(01)00302-0

upstream raw materials:

(3S,4S)-(+)-1-benzyl-3,4-pyrrolidinediol

tert-butyldimethylsilyl chloride

(3R,4R)-1-benzyl-3,4-dihydroxypyrrolidine-2,5-dione

benzylamine

Downstream raw materials:

C₁₈H₂₆N₂O₄

tert-butyl (3R,4S)-4-(tert-butyldimethylsilyloxy)-1-((2S)-2-(1-(6-fluoro-3'-methylbiphenyl-2-yl)-5-methoxypentyl)morpholine-4-carbonyl)pyrrolidin-3-ylcarbamate

(3R,4S)-1-benzyl-3-(tert-butoxycarbonylamino)-4-(tert-butyldimethyl-silyloxy)pyrrolidine

(3R,4S)-1-benzyl-3-amino-4-(tert-butyldimethylsilyloxy)pyrrolidine