Boron tribromide → (+/-)-rel-1-(3-fluoro-4-methylbenzyl)-3-((3S,4S)-3-hydroxy-4-(4-hydroxyphenyl)piperidin-1-yl)pyrrolidin-2-one

Participants

Reaction Steps

To a solution of (±)-rel-1-(3-fluoro-4-methylbenzyl)-3-((3S,4S)-3-hydroxy-4-(4-methoxyphenyl)piperidin-1-yl)pyrrolidin-2-one (300 mg, 0.73 mmol) in DCM (20 mL) under nitrogen at −10° C. was added boron tribromide (0.17 mL, 1.8 mmol) and the reaction mixture was stirred at rt for 1 h. The reaction was then quenched with saturated sodium bicarbonate solution and extracted with 200 mL of ethyl acetate. The organic layer was separated, dried over Na2SO4, filtered, and evaporated under reduced pressure to give (±)-rel-1-(3-fluoro-4-methylbenzyl)-3-((3S,4S)-3-hydroxy-4-(4-hydroxyphenyl)piperidin-1-yl)pyrrolidin-2-one (290 mg, 0.36 mmol, 50% yield, mixture of 4 diastereoisomers); LCMS (Method F) RT 1.854 min m/z 399.2 (M+H+).

Provenance & Evidence