Carbon Dioxide → 1-(5-Acetoxy-6-bromohexyl)-3,7-dimethylxanthine

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Reaction Steps

To 1-(5,6-dihydroxyhexyl)-3,7-dimethylxanthine 1.0 g, 3.38 mmol) was added 30% hydrogen bromide-acetic acid (3.4 mL) over 30 seconds and then stirred for 2.5 hours until all of the solid dissolved. The solution was poured carefully over a mixture of sodium bicarbonate (12 g) and ice water (50 mL). After carbon dioxide evolution had subsided, the mixture was extracted with dichloromethane (3×25 mL). The combined extracts were dried over magnesium sulfate and the solvent evaporated under vacuum, yielding 1.3 g (3.24 mmol, 96%) 1-(5-Acetoxy-6-bromohexyl)-3,7-dimethylxanthine as a viscous oil, dissolved in methanol (5 mL). A 1M sodium methoxide in methanol solution (3.9 mL) was added over 30 seconds. After stirring for 20 minutes, the solution was reated with water (20 mL) and then extracted with dichloromethane (3×15 mL). The combined extracts were dried over magnesium sulfate and the solvents were evaporated under vacuum to yield 900 mg (3.24 mmol, 100% yield) 1-(5,6-Oxidohexyl)-3,7-dimethylxanthine as white crystals.

Provenance & Evidence