Water → 1-(16,17-Dihydroxyheptadecyl)-3,7-dimethylxanthine

Participants

Reaction Steps

A solution of 1.5 g of 1-(16-Heptadecenyl)-3,7-dimethylxanthine (3.60 mmol), 4-methylmorpholine-N-oxide (1.83 ml, 60% wt in water, 10.6 mmol) and potassium osmate dihydrate (16 mg, 0.04 mmol) in acetone/water/tetrahydrofuran (10:7:5, 110 ml) was stirred for 60 hours. Water (100 ml) and sodium sulfite (1 g) were added and the resulting reaction mixture stirred for 1 hour. The reaction mixture was extracted with dichloromethane (2×100 ml) and the organic phase dried over magnesium sulfate. The evaporated solvent left a cream-colored solid. Recrystallization of the crude solid from hot ethyl acetate produced 1.31 g of 1-(16,17-dihydroxyheptadecyl)-3,7-dimethylxanthine as a white solid (81% yield).

Provenance & Evidence