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

Participants

Role	Name	HCID	Charge
Reactant	Water	HCID 962	—
Reactant	Sodium Dithionite	HCID 24489	—
Reactant	Methyl morpholine oxide	HCID 82029	—
Reactant	1-(Hex-5-en-1-yl)-3,7-dimethyl-3,7-dihydro-1H-purine-2,6-dione	HCID 12877680	—
Catalyst	tert-Butanol	HCID 6386	—
Catalyst	Osmium Tetroxide	HCID 30318	—
Solvent	Acetone	HCID 180	—
Product	1-(5,6-Dihydroxyhexyl)-3,7-dimethylxanthine	HCID 15895955	62%

Reaction Steps

To 1-(5-hexenyl)-3,7-dimethylxanthine (1.07 g, 4.1 mmol) and 4-methylmorpholine-N-oxide (1.44 g, 12.3 mmol) in water (20 ml) and acetone (10 ml) was added 2.5% solution of 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 was extracted with 25% ethanol-dichloromethane (3×30 ml). The combined extracts were dried over magnesium sulfate and the solvents were evaporated under vacuum to give 1-(5,6-dihydroxyhexyl)-3,7-dimethylxanthine (750 mg, 62% yield) as a white powder.

Provenance & Evidence

DOI	10.6084/m9.figshare.5104873.v1
Patent number	US05470878
Source dataset	uspto-grants-1995_11
ORD ID	ord-07d34b88f49b4dd680b55cfa6933b0b9
Source note	uspto-grants-1995_11