169750-17-8 | 3-FLUOROPYRROLIDINE HYDROCHLORIDE

CAS:169750-17-8 | 3-FLUOROPYRROLIDINE HYDROCHLORIDE,Description

3-Fluoropyrrolidine hydrochloride is a fluorinated chiral pyrrolidine salt, with a fluorine substituent on the R configured chiral carbon centre. It is used as a building block for the preparation of fluorinated pyrrolidine derivatives of cyclohexylglycine amides as potential inhibitors for dipeptidyl peptidase IV.

Synthesis Analysis

Ionic liquids based on 3-Fluoropyrrolidine hydrochloride can be synthesized by alkylation to the secondary amine. This is then followed by a quarterisation reaction of the amine with N-methyl bis (fluorosulfonyl)imide.

Molecular Structure Analysis

The molecular formula of 3-Fluoropyrrolidine hydrochloride is C4H9ClFN. The molecular weight is 125.57 g/mol.

Chemical Reactions Analysis

3-Fluoropyrrolidine hydrochloride can be used as a substrate in the preparation of imidazo[1,2-a]pyrazine derivatives as possible aurora kinase inhibitors and pyrazolopyrimidine derivatives as possible PDE10A inhibitors.

Physical And Chemical Properties Analysis

3-Fluoropyrrolidine hydrochloride is a solid at 20 degrees Celsius. It is air sensitive and hygroscopic.

Scientific Research Applications

• 3-Fluoropyrrolidine hydrochloride is a chemical compound with the molecular formula C4H9ClFN . It is available in the form of white to brown or pale pink crystals or powder. It has a melting point of 178.0-187.0°C.
• This compound can be employed as a building block for the preparation of various derivatives. For example, it can be used to prepare fluorinated pyrrolidine derivatives of cyclohexylglycine amides, which have potential as inhibitors for dipeptidyl peptidase IV. It can also be used to prepare fluoropyrrolidine containing N-ethylurea pyrazole derivatives, which are potential and selective inhibitors for Trypanosoma brucei and Trypanosoma cruzi, the parasitic causative agents of certain diseases.

• Ionic Liquids

  • Field: Chemistry
  • Application: Ionic liquids based on ®-(-)-3-Fluoropyrrolidine hydrochloride can be synthesized by alkylation to the secondary amine. This is followed by a quarterisation reaction of the amine with N-methyl bis(fluorosulfonyl)imide.
  • Results: The ionic liquids show high oxidation stability (> 5.5 V vs Li+/Li) and good high voltage cyclability up to 4.7 V.

• Perovskite Switching Metal Complex

  • Field: Materials Science
  • Application: A perovskite switching metal complex of CdCl2 (cadmium chloride) and methylated ®-(-)-3-Fluoropyrrolidine has exhibited dual-phase transitions of switchable dielectric constants at 370 and 460 K.
  • Results: Enantiomorphic perovskite ferroelectrics, ®-(-)-3-fluoropyrrolidium MnBr3 and (S)-(+)-3-fluoropyrrolidium MnBr3 display circular polarized luminescence.

• Aurora Kinase Inhibitors

  • Field: Medicinal Chemistry 
  • Application: ®-(-)-3-Fluoropyrrolidine hydrochloride may be used as a substrate in the preparation of Imidazo[1,2-a]pyrazine derivatives.
  • Results: These derivatives are potential aurora kinase inhibitors.

• PDE10A Inhibitors

  • Field: Medicinal Chemistry 
  • Application: ®-(-)-3-Fluoropyrrolidine hydrochloride may be used as a substrate in the preparation of Pyrazolopyrimidine derivatives.
  • Results: These derivatives are potential PDE10A Inhibitors.

• Imidazo[1,2-a]pyrazine Derivatives

  • Field: Medicinal Chemistry 
  • Application: ®-(-)-3-Fluoropyrrolidine hydrochloride may be used as a substrate in the preparation of Imidazo[1,2-a]pyrazine derivatives.
  • Results: These derivatives are potential aurora kinase inhibitors.

• Pyrazolopyrimidine Derivatives

  • Field: Medicinal Chemistry 
  • Application: ®-(-)-3-Fluoropyrrolidine hydrochloride may be used as a substrate in the preparation of Pyrazolopyrimidine derivatives.
  • Results: These derivatives are potential PDE10A Inhibitors.

Safety And Hazards

This chemical is considered hazardous by the 2012 OSHA Hazard Communication Standard (29 CFR 1910.1200). It is harmful if swallowed, causes skin irritation, causes serious eye irritation, and may cause respiratory irritation. It should be stored under inert gas in a well-ventilated place and the container should be kept tightly closed.

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