Boron tribromide → HCID 118207292, compound

Participants

Reaction Steps

To a solution of 3-(3,3-difluoro-4-(4-methoxyphenyl)piperidin-1-yl)-1-(4-fluorobenzyl)pyrrolidin-2-one (200 mg, 0.48 mmol, mixture of diastereomers from step D) in DCM (15 mL) at −10° C. was added boron tribromide (0.05 mL, 0.48 mmol) and the reaction mixture was stirred under nitrogen for one hour. The mixture was then diluted with a satd. sodium bicarbonate solution and extracted with 100 mL of DCM. The organic layer was separated, dried over Na2SO4, filtered, and evaporated under reduced pressure. The residue was purified via preparative HPLC (method D) to yield 3-(3,3-difluoro-4-(4-hydroxyphenyl)-piperidin-1-yl)-1-(4-fluorobenzyl)pyrrolidin-2-one (mixture of 4 diastereomers, 34 mg, 17% yield). LCMS (method N) RT 1.497 min, m/z 405.0 (M+H+).

Provenance & Evidence