1-benzyloxycarbonyl-(2R)-tert-butyldimethylsilyloxymethyl-(3S)-hydroxypyrrolidine

Base Information

• Chemical Name: 1-benzyloxycarbonyl-(2R)-tert-butyldimethylsilyloxymethyl-(3S)-hydroxypyrrolidine
• CAS No.: 441718-01-0
• Molecular Formula: C₁₉H₃₁NO₄Si
• Molecular Weight: 365.545
• Mol file: 441718-01-0.mol

Synonyms:1-benzyloxycarbonyl-(2R)-tert-butyldimethylsilyloxymethyl-(3S)-hydroxypyrrolidine

Chemical Property of 1-benzyloxycarbonyl-(2R)-tert-butyldimethylsilyloxymethyl-(3S)-hydroxypyrrolidine

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of 1-benzyloxycarbonyl-(2R)-tert-butyldimethylsilyloxymethyl-(3S)-hydroxypyrrolidine

There total 4 articles about 1-benzyloxycarbonyl-(2R)-tert-butyldimethylsilyloxymethyl-(3S)-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: 90.0%

1-benzyloxycarbonyl-(3S)-hydroxy-(2R)-pyrrolidinemethanol + tert-butyldimethylsilyl chloride (18162-48-6) → 1-benzyloxycarbonyl-(2R)-tert-butyldimethylsilyloxymethyl-(3S)-hydroxypyrrolidine (441718-01-0)

Guidance literature:

With triethylamine; In dichloromethane; at 0 - 20 ℃; for 48h;

DOI:10.1016/j.bmc.2012.11.003

Reference yield:

(2S,3S)-1-((benzyloxy)carbonyl)-3-hydroxypyrrolidine-2-carboxylic acid (62182-54-1) → 1-benzyloxycarbonyl-(2R)-tert-butyldimethylsilyloxymethyl-(3S)-hydroxypyrrolidine (441718-01-0)

Guidance literature:

Multi-step reaction with 3 steps

1: sulfuric acid / Reflux

2: lithium borohydride / tetrahydrofuran / 0 °C

3: triethylamine; 1,8-diazabicyclo[5.4.0]undec-7-ene / dichloromethane

With lithium borohydride; sulfuric acid; 1,8-diazabicyclo[5.4.0]undec-7-ene; triethylamine; In tetrahydrofuran; dichloromethane;

Reference yield:

1-benzyl 2-methyl(2S,3S)-3-hydroxypyrrolidine-1,2-dicarboxylate → 1-benzyloxycarbonyl-(2R)-tert-butyldimethylsilyloxymethyl-(3S)-hydroxypyrrolidine (441718-01-0)

Guidance literature:

Multi-step reaction with 2 steps

1: lithium borohydride / tetrahydrofuran / 0 °C

2: triethylamine; 1,8-diazabicyclo[5.4.0]undec-7-ene / dichloromethane

With lithium borohydride; 1,8-diazabicyclo[5.4.0]undec-7-ene; triethylamine; In tetrahydrofuran; dichloromethane;

upstream raw materials:

tert-butyldimethylsilyl chloride

(2S,3S)-1-((benzyloxy)carbonyl)-3-hydroxypyrrolidine-2-carboxylic acid

benzyl chloroformate

Downstream raw materials:

1-benzyloxycarbonyl-(2R)-tert-butyldimethylsilyloxymethyl-(3S)-methoxypyrrolidine

C₂₉H₃₃F₂N₃O₆

ethyl trans-4-[(3R)-methoxy-(2R)-pyrrolidinylmethoxy]cyclohexanecarboxylate

ethyl trans-4-[1-(tert-butoxycarbonyl)-(3R)-methoxy-(2R)-pyrrolidinylmethoxy]cyclohexanecarboxylate