Boron tribromide → HCID 118207320, compound

Participants

Reaction Conditions

Reaction Steps

A mixture of 3-(3,3-difluoro-4-(4-methoxyphenyl)piperidin-1-yl)-1-(4-methylbenzyl)pyrrolidin-2-one (230 mg, 0.55 mmol) and 4 mL DCM was cooled to −78° C., followed by the dropwise addition of boron tribromide (0.05 mL, 0.55 mmol). The mixture was then allowed to warm up to rt over 4 h. The reaction was then quenched with 50 mL of 10% aqueous sodium bicarbonate and extracted with 4×50 mL DCM. The combined organic fractions were dried over Na2SO4, filtered, and concentrated. The residue was subjected to preparative HPLC (method B) to afford 28.1 mg 3-(3,3-difluoro-4-(4-hydroxyphenyl)piperidin-1-yl)-1-(4-methylbenzyl)pyrrolidin-2-one as a mixture of 4 diastereomers. LCMS (method N) RT 1.59 min, m/z 401 (M+H+).

Provenance & Evidence