Sodium Thiosulfate → 1-(3-Methoxy-4-nitrophenyl)piperidin-4-one

Participants

Reaction Steps

Dess-Martin periodinane (13.62 g, 32.11 mmol) was added to 1-(3-methoxy-4-nitrophenyl)piperidin-4-ol (INTERMEDIATE 17, 5.4 g, 21.41 mmol) in DCM (120 mL) at 0° C. and the reaction mixture was stirred for 30 min. The reaction mixture was then allowed to warm to RT and stirred for an additional 4 h. The reaction solution was poured into a mixture of 20% aqueous Na2S2O3 (50 mL) and saturated aqueous NaHCO3 (50 mL) and the biphasic mixture was stirred at RT for 1 h. The mixture was partitioned and organic layer was washed with brine, dried over sodium sulfate, filtered and concentrated in vacuo. The crude residue was purified by chromatography on silica gel (5% MeOH/DCM) to give the title product (4.28 g, 80%). m/z 251.

Provenance & Evidence