(2S,5R)-5-benzyloxymetyl-1-tert-butoxycarbonyl-2-cyanopyrrolidine

Base Information

• Chemical Name: (2S,5R)-5-benzyloxymetyl-1-tert-butoxycarbonyl-2-cyanopyrrolidine
• CAS No.: 152500-23-7
• Molecular Formula: C₁₈H₂₄N₂O₃
• Molecular Weight: 316.4
• Mol file: 152500-23-7.mol

Synonyms:(2S,5R)-5-benzyloxymetyl-1-tert-butoxycarbonyl-2-cyanopyrrolidine

Chemical Property of (2S,5R)-5-benzyloxymetyl-1-tert-butoxycarbonyl-2-cyanopyrrolidine

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (2S,5R)-5-benzyloxymetyl-1-tert-butoxycarbonyl-2-cyanopyrrolidine

There total 21 articles about (2S,5R)-5-benzyloxymetyl-1-tert-butoxycarbonyl-2-cyanopyrrolidine 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: 66.0%

trimethylsilyl cyanide (7677-24-9) + (2S)-tert-butyl 2-(benzyloxymethyl)-5-methoxypyrrolidine-1-carboxylate → (2S,5R)-5-benzyloxymetyl-1-tert-butoxycarbonyl-2-cyanopyrrolidine (152500-23-7) + (2S,5S)-5-benzyloxymethyl-1-tert-butoxycarbonyl-2-cyanopyrrolidine (159516-84-4)

Guidance literature:

With boron trifluoride diethyl etherate; In dichloromethane; at -78 ℃; for 1h;

DOI:10.1016/S0040-4020(01)80643-8

Reference yield:

trimethylsilyl cyanide (7677-24-9) + (2S)-tert-butyl 2-(benzyloxymethyl)-5-methoxypyrrolidine-1-carboxylate → (2S,5S)-2-Benzyloxymethyl-5-cyano-pyrrolidine-1-carboxylic acid tert-butyl ester (152612-41-4) + (2S,5R)-5-benzyloxymetyl-1-tert-butoxycarbonyl-2-cyanopyrrolidine (152500-23-7)

Guidance literature:

With boron trifluoride diethyl etherate; In dichloromethane; at -78 ℃; Yield given;

DOI:10.1016/S0040-4039(00)73849-4

Reference yield:

di-tert-butyl dicarbonate (24424-99-5) → (2S,5R)-5-benzyloxymetyl-1-tert-butoxycarbonyl-2-cyanopyrrolidine (152500-23-7)

Guidance literature:

Multi-step reaction with 4 steps

1: 98 percent / 4-dimethylaminopyridine / acetonitrile; triethylamine / 3 h / Ambient temperature

2: diisobutylaluminium hydride / hexane; tetrahydrofuran / 1 h / -78 °C

3: pyridinium p-toluenesulfonate / 3 h / Ambient temperature

4: 29 percent / boron trifluoride etherate / CH₂Cl₂ / 1 h / -78 °C

With dmap; boron trifluoride diethyl etherate; pyridinium p-toluenesulfonate; diisobutylaluminium hydride; In tetrahydrofuran; hexane; dichloromethane; triethylamine; acetonitrile;

DOI:10.1016/S0040-4020(01)80643-8

upstream raw materials:

trimethylsilyl cyanide

L-glutamic acid

di-tert-butyl dicarbonate

benzyl bromide

Downstream raw materials:

(2R,5S)-1-benzyl-5-benzyloxymethyl-2-hydroxymethylpyrrolidine

(2R,5S)-5-benzyloxymethyl-2-hydroxymethylpyrrolidine

(2R,5S)-5-benzyloxymethyl-1-tert-butoxycarbonyl-2-formylpyrrolidine