tert-Butanol → 1-(8,9-Dihydroxynonyl)-3,7-dimethylxanthine

HRID 1637661Notes

Reaction equation

HRID 1637661 reaction equation
[CH2:1]([N:10]1[C:19](=[O:20])[C:18]2[N:17]([CH3:21])[CH:16]=[N:15][C:14]=2[N:13]([CH3:22])[C:11]1=[O:12])[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6]CC=C.C[N+]1([O-])CC[O:27]CC1.S(S([O-])=O)([O-])=O.[Na+].[Na+].[C:39]([OH:43])(C)([CH3:41])[CH3:40]>[Os](=O)(=O)(=O)=O.CC(C)=O.O>[OH:43][CH:39]([CH2:41][OH:27])[CH2:40][CH2:6][CH2:5][CH2:4][CH2:3][CH2:2][CH2:1][N:10]1[C:19](=[O:20])[C:18]2[N:17]([CH3:21])[CH:16]=[N:15][C:14]=2[N:13]([CH3:22])[C:11]1=[O:12]

Participants

8

Reactant 4

HCID 6386tert-ButanolHCID 24489Sodium DithioniteHCID 82029Methyl morpholine oxideHCID 152306351-(8-Nonenyl)-3,7-dimethylxanthine

Product 1

HCID 98408081-(8,9-Dihydroxynonyl)-3,7-dimethylxanthineYield 54%

Reagents, catalysts & solvents 3

HCID 30318Osmium TetroxideCatalystHCID 180AcetoneSolventHCID 962WaterSolvent

Procedure

A solution of 1-(8-nonenyl)-3,7-dimethylxanthine (810 mg, 2.7 mmol), prepared above, 4-methylmorpholine-N-oxide (340 mg, 2.9 mmol) and 3 drops of 2.5% osmium tetroxide in t-butanol, acetone (20 ml) and water (20 ml) was stirred for 24 hours, followed by addition of saturated aqueous sodium dithionite solution (5 ml). After stirring the resulting mixture for 15 minutes, the reaction mixture was extracted with four 50 ml aliquots of 25% ethanol-dichloromethane. The combined organic layers were dried over sodium sulfate, and the solvent evaporated under vacuum. A resulting solid residue was recrystallized in ethanol-chloroform, producing 490 mg of 1-(8,9-dihydroxynonyl)-3,7-dimethylxanthine (54% yield).

Workup

  1. stirringAfter stirring the resulting mixture for 15 minutes
  2. extractionthe reaction mixture was extracted with four 50 ml aliquots of 25% ethanol-dichloromethane
  3. dry with materialThe combined organic layers were dried over sodium sulfate
  4. customthe solvent evaporated under vacuum
  5. customA resulting solid residue was recrystallized in ethanol-chloroform

Sources & evidence

ORD record
ord-af92059b44e84ab392cdca91aa408d72
Source dataset
uspto-grants-2000_03
Patent number
US06043250

Reaction notes

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