tert-Butanol → 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 a 2.5% solution in t-butanol of osmium tetroxide (3 drops) in acetone (40 mL) and water (10 mL) was stirred for 24 hours. Following addition of 5 mL of a saturated solution of sodium dithionite and an additional 15 minutes of stirring, the reaction product was extracted with 25% ethanol/dichloromethane (4×50 mL). The combined organic portions were dried over sodium sulfate. The solvents were evaporated to a give a white solid residue. Upon recrystallization of the residue in ethanol, 3.30 g (93% yield) 1-(9,10-dihydroxydecyl)-3,7-dimethylxanthine (inventive compound no. 1564) were obtained.

Provenance & Evidence