Borane;tetrahydrofuran → HCID 57991895, compound

Participants

Reaction Conditions

Reaction Steps

To a stirred mixture of (2S,3S)-methyl 3-(4-(trifluoromethyl)phenyl)pyrrolidine-2-carboxylate (0.33 g, 1.21 mmol) in THF (5.0 mL) was added BH3-THF (12 mL, 12 mmol) at 0° C. The mixture was heated at reflux for 4 hours. The mixture was cooled to 0° C., the reaction carefully quenched with MeOH, and the mixture was evaporated in vacuo. The residue was diluted with saturated aqueous NaHCO3, water and extracted with EtOAc (3×50 mL). The combined organic layers were washed with brine, dried over Na2SO4, and concentrated. The crude residue was purified by flash column chromatography (ISCO Combiflash system, eluting with a gradient from pure DCM to 5% MeOH in DCM) to provide ((2S,3S)-3-(4-(trifluoromethyl)phenyl)pyrrolidin-2-yl)methanol as a white solid (45 mg, 15%).

Provenance & Evidence