tert-Butanol → 1-(9,10-dihydroxydecyl)-3,7-dimethylxanthine

HRID 2393347Notes

Reaction equation

HRID 2393347 reaction equation
[CH2:1]([N:11]1[C:20](=[O:21])[C:19]2[N:18]([CH3:22])[CH:17]=[N:16][C:15]=2[N:14]([CH3:23])[C:12]1=[O:13])[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7]CC=C.C[N+]1([O-])CC[O:28]CC1.S(S([O-])=O)([O-])=O.[Na+].[Na+].[C:40]([OH:44])(C)([CH3:42])[CH3:41]>[Os](=O)(=O)(=O)=O.CC(C)=O.O>[OH:44][CH:40]([CH2:42][OH:28])[CH2:41][CH2:7][CH2:6][CH2:5][CH2:4][CH2:3][CH2:2][CH2:1][N:11]1[C:20](=[O:21])[C:19]2[N:18]([CH3:22])[CH:17]=[N:16][C:15]=2[N:14]([CH3:23])[C:12]1=[O:13]

Participants

8

Reactant 4

HCID 6386tert-ButanolHCID 24489Sodium DithioniteHCID 82029Methyl morpholine oxideHCID 15230636HCID 15230636, compound

Product 1

HCID 98198951-(9,10-dihydroxydecyl)-3,7-dimethylxanthineYield 93%

Reagents, catalysts & solvents 3

HCID 30318Osmium TetroxideCatalystHCID 180AcetoneSolventHCID 962WaterSolvent

Procedure

1-(9-Decenyl)-3,7-dimethylxanthine (3.2 g, 10.1 mmol), 4-methylmorpholine-N-oxide (1.41 g, 12 mmol), 3 drops of 2.5% osmium tetroxide solution in t-butanol, acetone (40 ml) and water (10 ml) were stirred for 24 hours. Following addition of 5 ml of a saturated solution of sodium dithionite and a further 15 minutes of stirring, the reaction mixture was extracted with four 50 ml aliquots of 25% ethanol/dichloromethane. The combined organic portions were dried over sodium sulfate. Evaporating the solvents left a white solid residue, which upon recrystallization in ethanol produced 3.3 g of 1-(9,10-dihydroxydecyl)-3,7-dimethylxanthine (93% yield).

Workup

  1. extractionthe reaction mixture was extracted with four 50 ml aliquots of 25% ethanol/dichloromethane
  2. dry with materialThe combined organic portions were dried over sodium sulfate
  3. customEvaporating the solvents
  4. waitleft a white solid residue, which
  5. customupon recrystallization in ethanol

Sources & evidence

ORD record
ord-9190faab5b994c0596508264e329149a
Source dataset
uspto-grants-1998_09
Patent number
US05807862

Reaction notes

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