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

HRID 356614

Reaction equation

HRID 356614 reaction equation
[CH2:1]([N:7]1[C:16](=[O:17])[C:15]2[N:14]([CH3:18])[CH:13]=[N:12][C:11]=2[N:10]([CH3:19])[C:8]1=[O:9])[CH2:2][CH2:3][CH2:4][CH:5]=[CH2:6].C[N+]1([O-])CC[O:24]CC1.S(S([O-])=O)([O-])=O.[Na+].[Na+].[OH2:36]>CC(C)=O.C(O)(C)(C)C.[Os](=O)(=O)(=O)=O>[OH:36][CH:5]([CH2:6][OH:24])[CH2:4][CH2:3][CH2:2][CH2:1][N:7]1[C:16](=[O:17])[C:15]2[N:14]([CH3:18])[CH:13]=[N:12][C:11]=2[N:10]([CH3:19])[C:8]1=[O:9]

Participants

8

Reactant 4

HCID 962WaterHCID 24489Sodium DithioniteHCID 82029Methyl morpholine oxideHCID 128776801-(Hex-5-en-1-yl)-3,7-dimethyl-3,7-dihydro-1H-purine-2,6-dione

Product 1

HCID 158959551-(5,6-Dihydroxyhexyl)-3,7-dimethylxanthineYield 62%

Reagents, catalysts & solvents 3

HCID 6386tert-ButanolCatalystHCID 30318Osmium TetroxideCatalystHCID 180AcetoneSolvent

Procedure

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.

Workup

  1. waitAfter 2 minutes
  2. extractionthe mixture was extracted with 25% ethanol-dichloromethane (3×30 ml)
  3. dry with materialThe combined extracts were dried over magnesium sulfate
  4. customthe solvents were evaporated under vacuum

Sources & evidence

ORD record
ord-30d30cd5c01b4f508e5969973ef1199e
Source dataset
uspto-grants-1998_11
Patent number
US05837703

Linked notes

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