3,3-DIFLUOROPYRROLIDINE HYDROCHLORIDE Chemical Properties

Melting point:

128-130°C

storage temp. 

Inert atmosphere,Room Temperature

form 

solid

color 

White to off white

Sensitive 

Hygroscopic

InChI

InChI=1S/C4H7F2N.ClH/c5-4(6)1-2-7-3-4;/h7H,1-3H2;1H

InChIKey

YYVPZQADFREIFR-UHFFFAOYSA-N

SMILES

N1CCC(F)(F)C1.[H]Cl

CAS DataBase Reference

163457-23-6(CAS DataBase Reference)

Safety Information

Hazard Codes 

Xi

Risk Statements 

36/37/38

Safety Statements 

26-36/37/39

WGK Germany 

3

Hazard Note 

Irritant

HazardClass 

IRRITANT, HYGROSCOPIC

HS Code 

29339900

MSDS

• Language:English Provider:ALFA

3,3-DIFLUOROPYRROLIDINE HYDROCHLORIDE Usage And Synthesis

Chemical Properties

Beige solid

Uses

3,3-Difluoropyrrolidine hydrochloride can be used as a building block in the synthesis of:

• Triazole substituted prolyl difluoropyrrolidines as potential inhibitors of dipeptidyl peptidase-4.
• Dual leucine zipper kinase (DLK) inhibitors.

It can be also used as a reactant in the preparation of cyclic and acyclic β-aminofluoroalkenes via allylic amination using the Pd catalyst.

Synthesis

Part C: 1,1-dimethylethyl 3,3-difluoropyrrolidine-1-carboxylate (0.868 g, 4.19 mmol) was dissolved in 1.5 mL of 1,4-dioxane and cooled to 0°C. A 1,4-dioxane solution (11 mL, 44 mmol) of 4 M hydrogen chloride was slowly added with stirring. The reaction mixture was continued to be stirred at 0°C for 40 minutes, then brought to room temperature and stirred for 1 hour. Upon completion of the reaction, the solvent was removed by concentration under reduced pressure to afford 0.65 g of 3,3-difluoropyrrolidine hydrochloride (100% yield). The product was characterized by 1H-NMR (CD3OD): δ 3.54 (2H, t, J = 11.9 Hz), 3.43 (2H, t, J = 7.8 Hz), 2.40 (2H, m).

References

[1] Patent: US2004/186134, 2004, A1. Location in patent: Page 241
[2] Patent: US2018/237472, 2018, A1. Location in patent: Paragraph 0170; 0171
[3] Patent: WO2017/17630, 2017, A1. Location in patent: Page/Page column 57

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