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

Temperature

0 °C

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).

1. additionAfter complete addition
2. temperatureto warm up to room temperature
3. stirringstirred for 18 hours
4. customThe reaction mixture was quenched with a 50/50 of a saturated aqueous solution of sodium bicarbonate
5. extractionThe aqueous layer was extracted 3 times with dichloromethane
6. washThe combined organic layers were washed with brine
7. dry with materialdried over magnesium sulfate
8. concentrationconcentrated in vacuo
9. customThe residue was purified on silica gel by flash column chromatography

ORD record

ord-0510502a331d41558cabe1313a6f3131

Source dataset

uspto-grants-2013_06

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08461149B2