Theobromine → 1-(7-Octenyl)-3,7-dimethylxanthine

Participants

Reaction Steps

1-(7,8-Dihydroxyoctyl)-3,7-dimethylxanthine (CT1538) was used as an intermediate for the synthesis of CT1514 (example 15). To a suspension of sodium hydride (580 mg, 24.2 mmol) in dimethylsulfoxide (100 ml) was added theobromine (3.96 g, 22.0 mmol). After stirring for 30 min, 8-bromo-1-octene (3.96 g, 22 mmol) was added and the mixture was stirred for 16 hr. The mixture was poured into water (200 ml) and extracted with dichloromethane (3×50 ml). The combined organic layers were washed with saturated aqueous sodium chloride solution (50 ml), dried over sodium sulfate, and the solvent was evaporated under vacuum to give 1-(7-octenyl)-3,7-dimethylxanthine (CT1535) (6.22 g, 97% yield) as an oil which solidified upon standing.

Provenance & Evidence