Water → 1-(8,9-Dihydroxynonyl)-3,7-dimethylxanthine

Participants

Reaction Steps

A solution of 1-(8-nonenyl)-3,7-dimethylxanthine (CT1550 810 mg, 2.9 mmol), 4-methylmorpholine-N-oxide (340 mg, 2.9 mmol) and OsO4 (3 drops of a 2.5% solution by weight in tBuOH) in acetone (20 ml) and water (20 ml) was stirred for 24 hrs. A saturated solution of sodium dithionite (5 ml) was added to the reaction mixture which was then stirred for 15 min. The reaction mixture was extracted with 25% EtOH/dichloromethane (4×50 ml). The organic layers were combined, dried with sodium sulfate and evaporated to a white solid which was recrystalized in ethanol/chloroform to give 1-(8,9-dihydroxynonyl)-3,7-dimethylxanthine (CT 1561 ) (490 mg, 54% yield).

Provenance & Evidence