(R)-3-Fluoropyrrolidine

Base Information

• Chemical Name: (R)-3-Fluoropyrrolidine
• CAS No.: 679431-51-7
• Molecular Formula: C4H9FN
• Molecular Weight: 89.1126
• DSSTox Substance ID: DTXSID90987336
• Wikidata: Q72476885
• Mol file: 679431-51-7.mol

Synonyms:(R)-3-FLUOROPYRROLIDINE;679431-51-7;(3R)-3-fluoropyrrolidine;(R)-3-fluoro-pyrrolidine;Pyrrolidine, 3-fluoro-, (3R)-;C4H8FN;(R)-3-fluoropyrrolidin;(3R)-3-fluoro-pyrrolidin;DTXSID90987336;CDDGNGVFPQRJJM-SCSAIBSYSA-N;MFCD06738462;AKOS006282050;AKOS015852400;CS-0053326;EN300-154034;P10397

Chemical Property of (R)-3-Fluoropyrrolidine

Chemical Property:

• Boiling Point: 91.0±33.0 °C(Predicted)
• PKA: 8.68±0.10(Predicted)
• PSA: 12.03000
• Density: 0.99±0.1 g/cm3(Predicted)
• LogP: 0.64660
• Storage Temp.: under inert gas (nitrogen or Argon) at 2–8 °C
• XLogP3: 0.3
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 2
• Rotatable Bond Count: 0
• Exact Mass: 89.064077422
• Heavy Atom Count: 6
• Complexity: 46.8

Purity/Quality:

98%min ^*data from raw suppliers

(3R)-3-Fluoropyrrolidine 96% ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: C1CNCC1F
• Isomeric SMILES: C1CNC[C@@H]1F

Technology Process of (R)-3-Fluoropyrrolidine

There total 2 articles about (R)-3-Fluoropyrrolidine 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:

tert-butyl (S)-3-fluoropyrrolidine-1-carboxylate (479253-00-4) → (3R)-3-fluoropyrrolidine (679431-51-7,116574-74-4)

Guidance literature:

With hydrogenchloride; In 1,4-dioxane; at 0 - 20 ℃; for 2h;

Reference yield:

(R)-benzyl 3-fluoropyrrolidine-1-carboxylate (163457-21-4) → (3R)-3-fluoropyrrolidine (679431-51-7,116574-74-4)

Guidance literature:

With hydrogen; palladium on activated charcoal; In ethanol;

DOI:10.1016/j.bmcl.2003.12.040

Reference yield: 91.4%

methyl 4-(((3R,5S)-4-(4-(chloromethyl)benzoyl)-3,5-dimethylpiperazin-1-yl)methyl)benzoate + (3R)-3-fluoropyrrolidine (679431-51-7,116574-74-4) → methyl 4-(((3R,5S)-4-(4-(((R)-3-fluoropyrrolidin-1-yl)methyl)benzoyl)-3,5-dimethylpiperazin-1-yl)methyl)benzoate

Guidance literature:

With caesium carbonate; In acetonitrile; at 20 ℃; for 17h;

upstream raw materials:

(R)-benzyl 3-fluoropyrrolidine-1-carboxylate

tert-butyl (S)-3-fluoropyrrolidine-1-carboxylate

Downstream raw materials:

{(S)-6-[4-((R)-3-fluoro-pyrrolidin-1-yl)-benzenesulfonylamino]-1,2,3,4-tetrahydro-naphthalen-2-yl}-propyl-carbamic acid tert-butylester

C₁₈H₂₇FN₂O

C₁₉H₂₉FN₂O

C₁₉H₂₁Br₂FN₂O₂S

Refernces

• 1、 Caldwell, Charles G.,Chen, Ping,He, Jiafang,Parmee, Emma R.,Leiting, Barbara,Marsilio, Frank,Patel, Reshma A.,Wu, Joseph K.,Eiermann, George J.,Petrov, Aleksandr,He, Huaibing,Lyons, Kathryn A.,Thornberry, Nancy A.,Weber, Ann E.. "Fluoropyrrolidine amides as dipeptidyl peptidase IV inhibitors". . p. 1265 - 1268. Retrieved 2007/10/03.