Water → 1-(5,6-Dihydroxyhexyl)-3,7-dimethylxanthine

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Reaction Steps

To a mixture of 1-(5-Hexenyl)-3,7-dimethylxanthine (1.07 g, 4.1 mmol) and N-methylmorpholine-N-oxide (1.44 g, 12.3 mmol) in water (20 mL) and acetone (10 mL) was added 2.5% osmium tetraoxide in t-butanol (6 drops). After stirring for 48 hours, the mixture was treated with 20% aqueous sodium dithionite solution (20 mL). After 2 minutes, the mixture is extracted with 25% ethanol-dichloromethane solution (3×30 mL). The combined extracts were dried over magnesium sulfate and the solvents were evaporated under vacuum, yielding 750 mg, 2.53 mmol (62% yield) 1-(5,6-dihydroxyhexyl)-3,7-dimethylxanthine (inventive compound no. 1502) as a white powder.

Provenance & Evidence