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

Participants

Reaction Steps

A solution of 1-(16-Heptadecenyl)-3,7-dimethylxanthine (1.50 g, 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 reaction mixture stirred for 1 hour. The reaction mixture was extracted with dichloromethane (2×100 mL) and the organic phase dried using magnesium sulfate and the solvent evaporated to afford a cream solid. Recrystallization from hot ethyl acetate yields 1.31 g (81% yield) of 1-(16,17-dihydroxyheptadecyl)-3,7-dimethylxanthine (inventive compound no. 3514).

Provenance & Evidence