(R)-2-(2,5-Difluorophenyl)pyrrolidine hydrochloride

Uses

(R)-2-(2,5-Difluorophenyl)pyrrolidine hydrochloride is a fine chemical that is useful as a building block in the synthesis of complex compounds.

Mechanism of action

In medicinal chemistry, (R)-2-(2,5-DIFLUOROPHENYL)PYRROLIDINE HYDROCHLORIDE may interact with molecular targets such as enzymes, receptors, or ion channels, modulating their activity and leading to therapeutic effects. The presence of fluorine atoms can enhance the compound's binding affinity and selectivity for its target, contributing to its efficacy and potency.

Synthesis

The general procedure for the synthesis of (R)-2-(2,5-difluorophenyl)pyrrolidine hydrochloride from the compound (CAS: 1443538-31-5) was as follows: to a stirred solution of (R)-1-((S)-tert-butylsulfinyl)-2-(2,5-difluorophenyl)pyrrolidine (15 g, 52.19 mmol) in dioxane (25 mL) was added a 4 M HCl to a solution of dioxane (75 mL). The reaction mixture was stirred continuously at 20-35°C for 4 hours. Upon completion of the reaction, the mixture was concentrated under reduced pressure to give the crude product. The crude product was purified by washing with ether to give 7.5 g of (R)-2-(2,5-difluorophenyl)pyrrolidine hydrochloride as a white solid. Mass spectrometry (ESI) analysis showed: m/z 184 (M + H).

References

[1] Patent: WO2013/88256, 2013, A1. Location in patent: Page/Page column 59
[2] Patent: US2014/371217, 2014, A1. Location in patent: Paragraph 0561
[3] Patent: US2015/5280, 2015, A1. Location in patent: Paragraph 0527 - 0529
[4] Patent: US2015/368238, 2015, A1. Location in patent: Paragraph 0574; 0579