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

HRID 1955956Notes

Reaction equation

HRID 1955956 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+]>CC(O)(C)C.CC(C)=O.O=[Os](=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 30318Osmium TetroxideCatalystHCID 180AcetoneSolventHCID 6386tert-ButanolSolvent

Procedure

A solution of (1-(9-decenyl)-3,7-dimethylxanthine (3.2 g, 10.1 mmol)), 4-methylmorpholine-N-oxide (1.41 g, 12 mmol) and OsO4 (3 drops of a 2.5% solution by weight in tBuOH) in acetone (40 ml) and water (10 ml) was stirred for 24 hours. A saturated solution of sodium dithionite (5 ml) was added to the reaction mixture which was then stirred for 15 minutes. The reaction mixture was extracted with 25 % EtOH/dichloromethane (4×50 ml). The organic layers were combined, dried with sodium sulfate and evaporated to a white solid, which upon recrystalization in ethanol yielded 3.3 g of 1-(9,10-dihydroxydecyl)-3,7-dimethylxanthine (93% yield).

Workup

  1. extractionThe reaction mixture was extracted with 25 % EtOH/dichloromethane (4×50 ml)
  2. dry with materialdried with sodium sulfate
  3. customevaporated to a white solid, which upon recrystalization in ethanol

Sources & evidence

ORD record
ord-6df812a7420e493f817e5613fddcd8aa
Source dataset
uspto-grants-1998_07
Patent number
US05777115

Reaction notes

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