Acetone → HCID 10221386, compound

Participants

Reaction Steps

A solution of 1-(4-pentenyl)-3,7-dimethylxanthine (2.48 g, 10 mmol), 4-methylmorpholine-N-oxide (1.49 g, 12.7 mmol) and potassium osmate dihydrate (7.3 mg; 0.02 mmol) in acetone (20 mL) and water (5 mL) was stirred for 6 hours. A solution of 20% aqueous sodium sulphite (10 ml) was added and stirred for 30 minutes. The reaction mixture was extracted with 25% ethanol/dichloromethane (4×250 mL). The combined organic extracts were dried over anhydrous magnesium sulfate and concentrated under reduced pressure. The crude product obtained was further purified by flash chromatography over silica gel using ethyl acetate eluant to yield 2.5 g (88% yield) of 1-(4,5-dihydroxypentyl)-3,7-dimethylxanthine (inventive compound no. 1584).

Provenance & Evidence