(1R,2S)-2-(hydroxyphenylmethyl)pyrrolidine-1-carboxylic acid tert-butyl ester

Base Information

• Chemical Name: (1R,2S)-2-(hydroxyphenylmethyl)pyrrolidine-1-carboxylic acid tert-butyl ester
• CAS No.: 1266251-94-8
• Molecular Formula: C₁₆H₂₃NO₃
• Molecular Weight: 277.364
• Mol file: 1266251-94-8.mol

Synonyms:(1R,2S)-2-(hydroxyphenylmethyl)pyrrolidine-1-carboxylic acid tert-butyl ester

Chemical Property of (1R,2S)-2-(hydroxyphenylmethyl)pyrrolidine-1-carboxylic acid tert-butyl ester

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (1R,2S)-2-(hydroxyphenylmethyl)pyrrolidine-1-carboxylic acid tert-butyl ester

There total 16 articles about (1R,2S)-2-(hydroxyphenylmethyl)pyrrolidine-1-carboxylic acid tert-butyl 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: 99.0%

(S)-2-benzoylpyrrolidine-1-carboxylic acid tert-butyl ester (111492-61-6) → (1R,2S)-2-(hydroxyphenylmethyl)pyrrolidine-1-carboxylic acid tert-butyl ester (1266251-94-8)

Guidance literature:

With diisobutylaluminium hydride; In tetrahydrofuran; at 0 - 20 ℃; for 6h; Inert atmosphere;

DOI:10.1021/acs.joc.0c01764

Reference yield: 72.0%

(S)-2-benzoylpyrrolidine-1-carboxylic acid tert-butyl ester (111492-61-6) → (1S,2S)-2-(hydroxy(phenyl)methyl)pyrrolidine-1-carboxylic acid tert-butyl ester (913642-87-2) + (1R,2S)-2-(hydroxyphenylmethyl)pyrrolidine-1-carboxylic acid tert-butyl ester (1266251-94-8)

Guidance literature:

With sodium tetrahydroborate; In methanol; at 0 - 20 ℃; for 6h; Reagent/catalyst;

DOI:10.1021/acs.joc.0c01764

Reference yield: 68.0%

tert-butyl pyrrolidine-1-carboxylate (86953-79-9) + benzaldehyde (100-52-7) → (1S,2S)-2-(hydroxy(phenyl)methyl)pyrrolidine-1-carboxylic acid tert-butyl ester (913642-87-2) + (1R,2S)-2-(hydroxyphenylmethyl)pyrrolidine-1-carboxylic acid tert-butyl ester (1266251-94-8)

Guidance literature:

tert-butyl pyrrolidine-1-carboxylate; With isopropyllithium; (1R,5S,11aS)-3-methyldecahydro-1H-1,5-methanopyrido[1,2-a][1,5]diazocine; In diethyl ether; pentane; at -78 ℃; for 3h; Inert atmosphere;

benzaldehyde; In diethyl ether; pentane; at -78 - 20 ℃; for 16h; optical yield given as %ee; enantioselective reaction; Inert atmosphere;

DOI:10.1021/ja107672h

upstream raw materials:

di-tert-butyl dicarbonate

tert-butyl pyrrolidine-1-carboxylate

benzaldehyde

Boc-L-Pro-H

Downstream raw materials:

(S)-α-<(R)-pyrrolidin-2-yl>benzyl alcohol