Water → 1-(11,12-Dihydroxydodecyl)-3,7-dimethylxanthine

Participants

Reaction Steps

A solution of 1-(11-Dodecenyl)-3,7-dimethylxanthine (4.70 g, 13.6 mmol), 4-methylmorpholine-N-oxide (4.79 g, 40.7 mmol) and potassium osmate dihydrate (52 mg, 0.14 mmol) in acetone/water 1:2 (75 mL) was stirred for 16 hours. Water (50 mL) and sodium sulfite (5 g) were added and the mixture stirred for 1 hour. The reaction mixture was extracted with dichloromethane (3×100 mL), dried using magnesium sulfate and evaporated to obtain a pale green solid. Recrystallization from hot ethyl acetate yields 4.32 g (84% yield) 1-(11,12-dihydroxydodecyl)-3,7-dimethylxanthine (inventive compound no. 2517) as a white solid.

Provenance & Evidence