Trifluoroacetic acid → 3-(3-Chloro-5-fluorophenyl)pyrrolidin-3-ol

Participants

Reaction Steps

To a solution of tert-butyl 3-(3-chloro-5-fluorophenyl)-3-hydroxypyrrolidin-1-carboxylate (2.43 g, 7.7 mmol) in dichloromethane (80 mL), was added trifluoroacetic acid (5 mL). The mixture was stirred for 1.5 h after which the mixture was basified with aqueous sodium carbonate (10%, 50 mL) and evaporated. Ethyl acetate (100 mL) was added, the mixture was washed with brine and the organic phase was dried (MgSO4) and evaporated. Purification on a Biotage (solute SCX-3 SPE column (washed with methanol and eluted with methanol/triethylamine, 4:1), and by HPLC on Waters OBD 018, 5 μm (MeOH/33 mM NH3, 20:80 to 0:100), gave the title compound (1.07 g). MS m/z (rel. intensity, 70 eV) 215 (M+, bp), 157 (47), 129 (65), 109 (61), 95 (43).

Provenance & Evidence