1-Cyclohexyl-3,4-difluoropyrrolidine

Base Information

• Chemical Name: 1-Cyclohexyl-3,4-difluoropyrrolidine
• CAS No.: 209625-81-0
• Molecular Formula: C₁₀H₁₇F₂N
• Molecular Weight: 189.248
• DSSTox Substance ID: DTXSID10697667
• Mol file: 209625-81-0.mol

Synonyms:DTXSID10697667;1-cyclohexyl-3,4-difluoropyrrolidine;FT-0691011

Chemical Property of 1-Cyclohexyl-3,4-difluoropyrrolidine

Chemical Property:

• Boiling Point: 225.9±40.0 °C(Predicted)
• PKA: 6.04±0.60(Predicted)
• PSA: 3.24000
• Density: 1.07±0.1 g/cm3(Predicted)
• LogP: 2.24880
• XLogP3: 2.7
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 3
• Rotatable Bond Count: 1
• Exact Mass: 189.13290587
• Heavy Atom Count: 13
• Complexity: 158

Purity/Quality:

97% ^*data from raw suppliers

(3R,4R)-1-CYCLOHEXYL-3,4-DIFLUOROPYRROLIDINE 95.00% ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: C1CCC(CC1)N2CC(C(C2)F)F

Technology Process of 1-Cyclohexyl-3,4-difluoropyrrolidine

There total 6 articles about 1-Cyclohexyl-3,4-difluoropyrrolidine 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: 42.0%

(3S,4S)-1-cyclohexyl-3,4-bis(trifluoromethanesulfonyloxy)pyrrolidine (209625-82-1) → (3R,4R)-1-cyclohexyl-3,4-difluoropyrrolidine (209625-81-0)

Guidance literature:

With tetrabutyl ammonium fluoride; In tetrahydrofuran; at 20 ℃; for 20h;

DOI:10.1021/jo0513414

Reference yield:

(3R,4R)-1-cyclohexyl-3,4-diacetoxypyrrolidine-2,5-dione (209625-83-2) → (3R,4R)-1-cyclohexyl-3,4-difluoropyrrolidine (209625-81-0)

Guidance literature:

Multi-step reaction with 3 steps

1: 34 percent / sodium borohydride; iodine / tetrahydrofuran / Heating

2: triethylamine / CH₂Cl₂ / 16 h / 20 °C

3: 42 percent / tetra-n-butylammonium fluoride / tetrahydrofuran / 20 h / 20 °C

With sodium tetrahydroborate; tetrabutyl ammonium fluoride; iodine; triethylamine; In tetrahydrofuran; dichloromethane;

DOI:10.1021/jo0513414

Reference yield:

(3S,4S)-1-cyclohexylpyrrolidine-3,4-diol (90304-05-5) → (3R,4R)-1-cyclohexyl-3,4-difluoropyrrolidine (209625-81-0)

Guidance literature:

Multi-step reaction with 2 steps

1: triethylamine / CH₂Cl₂ / 16 h / 20 °C

2: 42 percent / tetra-n-butylammonium fluoride / tetrahydrofuran / 20 h / 20 °C

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

DOI:10.1021/jo0513414

upstream raw materials:

(3S,4S)-1-cyclohexyl-3,4-bis(trifluoromethanesulfonyloxy)pyrrolidine

cyclohexylamine

(3S,4S)-1-cyclohexylpyrrolidine-3,4-diol

(3R,4R)-1-cyclohexyl-3,4-diacetoxypyrrolidine-2,5-dione

Refernces

• 1、 Marson, Charles M.,Melling, Robert C.. "The first enantioselective syntheses of vicinal difluoropyrrolidines and the first catalytic asymmetric synthesis mediated by the C2 symmetry of a -CHFCHF- Unit". . p. 1223 - 1224. Retrieved 2007/10/03.