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

HRID 376246Notes

Reaction equation

HRID 376246 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][CH2:8][CH:9]=[CH2:10].C[N+]1([O-])CC[O:28]CC1.[OH2:32].S(S([O-])=O)([O-])=O.[Na+].[Na+]>C(O)(C)(C)C.CC(C)=O.[Os](=O)(=O)(=O)=O>[OH:32][CH:9]([CH2:10][OH:28])[CH2:8][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 962WaterHCID 24489Sodium DithioniteHCID 82029Methyl morpholine oxideHCID 15230636HCID 15230636, compound

Product 1

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

Reagents, catalysts & solvents 3

HCID 6386tert-ButanolCatalystHCID 30318Osmium TetroxideCatalystHCID 180AcetoneSolvent

Procedure

A solution of 1-(9-decenyl)-3,7-dimethylxanthine (3.2g, 10.1 mmol), prepared above, 4-methylmorpholine-N-oxide (1.41 g, 12 mmol) and 2.5% osmium tetroxide in t-butanol (3 drops) in acetone (40 ml) and water (10 ml) was stirred for 24 hr. After the addition of saturated sodium dithionite solution (5 ml) the mixture was stirred for 15 min. The mixture was extracted with 25% ethanol-dichloromethane (4×50 ml). The combined organic layers were dried over sodium sulfate and the solvents were evaporated under vacuum to give a solid which was recrystallized (ethanol) to give 1-(9,10-dihydroxydecyl)-3,7-dimethylxanthine (3.30 g, 93% yield).

Workup

  1. extractionThe mixture was extracted with 25% ethanol-dichloromethane (4×50 ml)
  2. dry with materialThe combined organic layers were dried over sodium sulfate
  3. customthe solvents were evaporated under vacuum
  4. customto give a solid which
  5. customwas recrystallized (ethanol)

Sources & evidence

ORD record
ord-3594cde333514c0e818f3644784f149c
Source dataset
uspto-grants-2000_02
Patent number
US06020337

Reaction notes

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