Triacetoxyperiodinane → tert-Butyl [(1R)-3-oxocyclopentyl]carbamate

Participants

Reaction Conditions

Reaction Steps

Dess-Martin periodinane (961 mg, 2.27 mmol) was added portionwise to a solution of tert-butyl (1R,3S)-3-hydroxycyclopentylcarbamate (380 mg, 1.89 mmol) in dichloromethane (10 mL) at 0° C. After complete addition, the reaction mixture was stirred for 1 hour at 0° C., then, allowed to warm up to room temperature and stirred for 18 hours. The reaction mixture was quenched with a 50/50 of a saturated aqueous solution of sodium bicarbonate and a saturated aqueous solution of sodium thiosulfate. The aqueous layer was extracted 3 times with dichloromethane. The combined organic layers were washed with brine, dried over magnesium sulfate and concentrated in vacuo. The residue was purified on silica gel by flash column chromatography to give the title compound (316 mg, 84% yield).

Provenance & Evidence