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

HRID 1870845Notes

Reaction equation

HRID 1870845 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]CC=C.C[N+]1([O-])CC[O:24]CC1.S(S([O-])=O)([O-])=O.[Na+].[Na+].[C:36]([OH:40])(C)([CH3:38])[CH3:37]>[Os](=O)(=O)(=O)=O.O.CC(C)=O>[OH:40][CH:36]([CH2:38][OH:24])[CH2:37][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 6386tert-ButanolHCID 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 30318Osmium TetroxideCatalystHCID 180AcetoneSolventHCID 962WaterSolvent

Procedure

Six drops of 2.5% osmium tetraoxide in t-butanol were added to a mixture of 1-(5-hexenyl)-3,7-dimethylxanthine (1.07 g, 4.1 mmol), as prepared above and N-methylmorpholine-N-oxide (1.44 g, 12.3 mmol) in water (20 ml) and acetone (10 ml). After stirring the resulting mixture for 48 hours, the mixture was treated with 20% aqueous sodium dithionite solution (20 ml). After 2 minutes, the mixture was extracted with three 30 ml aliquots of a 25% ethanol-dichloromethane solution. The combined extracts were dried over magnesium sulfate and the solvent was evaporated under vacuum, leaving 750 mg of a white powder, 1-(5,6-dihydroxyhexyl)-3,7-dimethylxanthine (2.53 mmol, 62% yield).

Workup

  1. waitAfter 2 minutes
  2. extractionthe mixture was extracted with three 30 ml aliquots of a 25% ethanol-dichloromethane solution
  3. dry with materialThe combined extracts were dried over magnesium sulfate
  4. customthe solvent was evaporated under vacuum

Sources & evidence

ORD record
ord-8d374ea87d6e4f6ca44a5d24d83a7eb4
Source dataset
uspto-grants-2000_08
Patent number
US06100271

Reaction notes

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