Water → 1-(7,8-Dihydroxyoctyl)-3,7-dimethylxanthine

Participants

Reaction Steps

A solution of 1-(7-octenyl)-3,7-dimethylxanthine (1.00 g, 4.5 mmol), prepared above, 4-methylmorpholine-N oxide (553 mg, 4.7 mmol), and 2.5% osmium tetroxide in t-butanol (3 drops) in acetone (25 ml) and water (20 ml) was stirred for 4 days. After addition of saturated aqueous sodium hydrosulfite solution (10 ml), the mixture was stirred for 30 min and water (50 ml) was added. The mixture was extracted with 20% ethanol-dichloromethane (3×50 ml) and the solvents were evaporated under vacuum to give a solid which was recrystallized (ethanol) to give 1-(7,8-dihydroxyoctyl)-3,7-dimethylxanthine (726 mg, 63% yield) as a white solid.

Provenance & Evidence