(Diethylamino)sulfur trifluoride → HCID 118207434, compound

Participants

Reaction Steps

To a solution of 1-(4-fluorobenzyl)-3-(trans-3-hydroxy-4-(4-methoxyphenyl)piperidin-1-yl)pyrrolidin-2-one from step B (2.5 g, 6.3 mmol) in 50 mL DCM was added DAST (4.1 mL, 31 mmol) and the reaction was stirred at ambient temperature for 1 h. The reaction was then quenched with a sat.bicarbonate solution (200 mL) and the mixture was extracted with 200 mL of DCM. The organic layer was dried over Na2SO4, filtered, and evaporated under reduced pressure. The residue was purified via silica gel chromatography eluting with 28% ethyl acetate in hexane to give (±)-rel-3-((3S,4S)-3-fluoro-4-(4-methoxyphenyl)piperidin-1-yl)-1-(4-fluorobenzyl)pyrrolidin-2-one (900 mg, 1.6 mmol) as a mixture of four diastereomers. LCMS (method P) RT 0.89 min, m/z 401.2 (M+H+).

Provenance & Evidence