Hydrochloric Acid → (R)-3-(5-hydroxyhexyl)-1,7-dimethylxanthine

To a stirring solution of (R)-3-(5-acetoxyhexyl)-1,7-dimethylxanthine (0.28 g, 0.87 mmol) in methanol (20 ml) was added an anhydrous solution of hydrogen chloride in ethyl ether (1 M, 2.6 ml, 2.6 mmol). After refluxing for 4 hours, the mixture was concentrated under reduced pressure. The residue was treated with saturated aqueous solution of sodium bicarbonate solution (30 ml) and extracted with dichloromethane (3×20 ml). The combined extracts were washed with saturated aqueous sodium chloride solution (30 ml), dried over sodium sulfate and concentrated under reduced pressure to give (R)-3-(5-hydroxyhexyl)-1,7-dimethylxanthine (0.20 g, 85% yield) as a colorless oil that solidified on standing.

1. temperatureAfter refluxing for 4 hours
2. concentrationthe mixture was concentrated under reduced pressure
3. additionThe residue was treated with saturated aqueous solution of sodium bicarbonate solution (30 ml)
4. extractionextracted with dichloromethane (3×20 ml)
5. washThe combined extracts were washed with saturated aqueous sodium chloride solution (30 ml)
6. dry with materialdried over sodium sulfate
7. concentrationconcentrated under reduced pressure

ORD record

ord-9c578a150c4b40a3929c902570fb2eed

Source dataset

uspto-grants-2005_04

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US06878715B1