Acetone → HCID 15885495, compound

Participants

Reaction Steps

A solution of 1-(10-undecenyl)-3,7-dimethylxanthine (4.3 g, 13 mmol), 4-methylmorpholine-N-oxide (1.942 g, 16.6 mmol) and potassium osmate dihydrate (9.5 mg; 0.026 mmol) in acetone (45 mL) and water (10 mL) was stirred for 6 hours. A solution of 20% aqueous sodium sulphite (12 ml) was added and stirred for 30 minutes. The reaction mixture was extracted with 25% ethanol/dichloromethane (4×100 mL). The combined organic extracts were dried over anhydrous magnesium sulfate, concentrated under reduced pressure and purified by flash chromatography over silica gel using methanol (5%)/dichloromethane eluant to yield 3.6 g (76% yield) 1-(10,11-dihydroxyundecanyl)-3,7-dimethylxanthine (inventive compound no. 1592).

Provenance & Evidence