Trifluoroacetic acid → 2-[2-(Trifluoromethyl)phenyl]pyrrolidine

Participants

Reaction Steps

To a solution of tert-butyl 2-hydroxy-2-(2-(trifluoromethyl)phenyl)pyrrolidine-1-carboxylate (I-27) (0.44 g, 1.6 mmol) in DCM (20 mL) was added TFA (10 mL). The reaction was stirred at room temperature until complete by LCMS then reduced to dryness. The crude mixture was dissolved in EtOH:AcOH (10:1, 8 mL) and was added NaCNBH3 (0.17 g, 2.7 mmol). The reaction was stirred for 1 hour then partitioned with EtOAc and saturated aqueous NaHCO3. The organic layer was separated, dried over MgSO4, filtered and reduced to dryness to afford 2-(2-(trifluoromethyl)phenyl)pyrrolidine (I-28) as a clear oil. MS m/z 216.1 (M+1)+.

Provenance & Evidence