Water → HCID 23287953, compound

Participants

Reaction Steps

To a mixture of N-(10-Undecenyl)-2-piperidone (4.00 g, 16 mmol) and a 60% aqueous solution of N-methylmorpholine-N-oxide (5 mL, 29 mmol) in water (10 mL) and acetone (20 mL) was added potassium osmate dihydrate (12 mg, 0.03 mmol). After stirring for 3 days, the mixture was treated with sodium dithionite (100 mg). After 30 minutes, dichloromethane (50 mL) and water (30 mL) were added and the organic layer separated. The aqueous layer was extracted with dichloromethane/10% methanol (2×70 mL). The combined organic extracts were dried over sodium sulfate and the solvents evaporated under vacuum. The residue was purified by chromatography using silica and ethyl acetate/methanol in a 0-20% gradient to yield 4.21 g (93%) N-(10,11-Dihydroxyundecyl)-2-piperidone (inventive compound no. 1617) as a colorless oil.

Provenance & Evidence