Water → 1-(9,10-dihydroxydecyl)-3,7-dimethylxanthine

Participants

Reaction Steps

A solution of (1-(9-decenyl)-3,7-dimethylxanthine (3.2 g, 10.1 mmol)), 4-methylmorpholine-N-oxide (1.41 g, 12 mmol) and OsO4 (3 drops of a 2.5% solution by weight in tBuOH) in acetone (40 ml) and water (10 ml) was stirred for 24 hours. A saturated solution of sodium dithionite (5 ml) was added to the reaction mixture which was then stirred for 15 minutes. The reaction mixture was extracted with 25 % EtOH/dichloromethane (4×50 ml). The organic layers were combined, dried with sodium sulfate and evaporated to a white solid, which upon recrystalization in ethanol yielded 3.3 g of 1-(9,10-dihydroxydecyl)-3,7-dimethylxanthine (93% yield).

Provenance & Evidence