(3R,4R)-benzyl 3,4-difluoropyrrolidine-1-carboxylate

Base Information

• Chemical Name: (3R,4R)-benzyl 3,4-difluoropyrrolidine-1-carboxylate
• CAS No.: 790658-58-1
• Molecular Formula: C₁₂H₁₃F₂NO₂
• Molecular Weight: 241.238
• DSSTox Substance ID: DTXSID60703803
• Wikidata: Q72516143
• Mol file: 790658-58-1.mol

Synonyms:790658-58-1;(3R,4R)-benzyl 3,4-difluoropyrrolidine-1-carboxylate;benzyl (3R,4R)-3,4-difluoropyrrolidine-1-carboxylate;(3R,4R)-N-CBZ-3,4-DIFLUOROPYRROLIDINE;(3R,4R)-Benzyl3,4-difluoropyrrolidine-1-carboxylate;DTXSID60703803;A9889;CS-0270040;EN300-28277160;rac-benzyl (3R,4R)-3,4-difluoropyrrolidine-1-carboxylate

Chemical Property of (3R,4R)-benzyl 3,4-difluoropyrrolidine-1-carboxylate

Chemical Property:

• Boiling Point: 333 ºC
• Flash Point: 155 ºC
• PSA: 29.54000
• Density: 1.26
• LogP: 2.25290
• Storage Temp.: 2-8°C
• XLogP3: 2.2
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 4
• Rotatable Bond Count: 3
• Exact Mass: 241.09143498
• Heavy Atom Count: 17
• Complexity: 259

Purity/Quality:

97% ^*data from raw suppliers

(3R,4R)-Benzyl 3,4-difluoropyrrolidine-1-carboxylate 95+% ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: C1C(C(CN1C(=O)OCC2=CC=CC=C2)F)F
• Isomeric SMILES: C1[C@H]([C@@H](CN1C(=O)OCC2=CC=CC=C2)F)F

Technology Process of (3R,4R)-benzyl 3,4-difluoropyrrolidine-1-carboxylate

There total 2 articles about (3R,4R)-benzyl 3,4-difluoropyrrolidine-1-carboxylate 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:

(3S,4S)-3,4-Bis-trifluoromethanesulfonyloxy-pyrrolidine-1-carboxylic acid benzyl ester → (3R,4R)-3,4-Difluoro-pyrrolidine-1-carboxylic acid benzyl ester (790658-58-1)

Guidance literature:

With tetrabutyl ammonium fluoride; In tetrahydrofuran;

DOI:10.1016/j.bmcl.2003.12.040

Reference yield:

(3S,4S)-N-benzyloxycarbonyl-3,4-dihydroxy-pyrrolidine (596793-30-5) → (3R,4R)-3,4-Difluoro-pyrrolidine-1-carboxylic acid benzyl ester (790658-58-1)

Guidance literature:

Multi-step reaction with 2 steps

1: pyridine / CH₂Cl₂

2: tetrabutylammonium fluoride / tetrahydrofuran

With pyridine; tetrabutyl ammonium fluoride; In tetrahydrofuran; dichloromethane;

DOI:10.1016/j.bmcl.2003.12.040

Reference yield:

(3R,4R)-3,4-Difluoro-pyrrolidine-1-carboxylic acid benzyl ester (790658-58-1) → trans-(R,R)-3,4-difluoropyrrolidine (863396-77-4)

Guidance literature:

With hydrogen; palladium on activated charcoal; In ethanol;

DOI:10.1016/j.bmcl.2003.12.040

upstream raw materials:

(3S,4S)-N-benzyloxycarbonyl-3,4-dihydroxy-pyrrolidine

Downstream raw materials:

trans-(R,R)-3,4-difluoropyrrolidine