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

HRID 1379013Notes

Reaction equation

HRID 1379013 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 (CT1563) (3.2g, 10.1 mmol), 4-methylmorpholine-N-oxide (1.41 g, 12 mmol) and 2.5% osmium tetraoxide 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 a give solid which was recrystallized (ethanol) to give 1-(9,10-dihydroxydecyl)-3,7-dimethylxanthine (CT1564) (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 to a give solid which
  4. customwas recrystallized (ethanol)

Sources & evidence

ORD record
ord-a0e33d7e03e6441fb5fe7a16f7e53dae
Source dataset
uspto-grants-1997_09
Patent number
US05670506

Reaction notes

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