Water → 1-(11,12-Dihydroxydodecyl)-3,7-dimethylxanthine

HRID 964545Notes

Reaction equation

HRID 964545 reaction equation
[CH2:1]([N:13]1[C:22](=[O:23])[C:21]2[N:20]([CH3:24])[CH:19]=[N:18][C:17]=2[N:16]([CH3:25])[C:14]1=[O:15])[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH:11]=[CH2:12].C[N+]1([O-])CC[O:30]CC1.[OH2:34].S([O-])([O-])=O.[Na+].[Na+]>CC(C)=O.O>[OH:34][CH:11]([CH2:12][OH:30])[CH2:10][CH2:9][CH2:8][CH2:7][CH2:6][CH2:5][CH2:4][CH2:3][CH2:2][CH2:1][N:13]1[C:22](=[O:23])[C:21]2[N:20]([CH3:24])[CH:19]=[N:18][C:17]=2[N:16]([CH3:25])[C:14]1=[O:15]

Participants

6

Reactant 4

HCID 962WaterHCID 24437Sodium SulfiteHCID 82029Methyl morpholine oxideHCID 23295871HCID 23295871, compound

Product 1

HCID 234356281-(11,12-Dihydroxydodecyl)-3,7-dimethylxanthineYield 84%

Reagents, catalysts & solvents 1

HCID 18366337Propan-2-one--water (1/1)Solvent

Procedure

A solution of 1-(11-dodecenyl)-3,7-dimethylxanthine, prepared above (4.70 g, 13.6 mmol), 4-methylmorpholine-N-oxide (4.79 g, 40.7 mmol) and potassium osmate dihydrate (52 mg, 0.14 mmol) in acetone/water 1:2 (75 ml) was stirred for 16 hours. Water (50 ml) and sodium sulfite (5 g) were subsequently added to the solution and the resulting reaction mixture stirred for 1 hour. The reaction mixture was extracted with dichloromethane (3×100 ml), dried using magnesium sulfate and the solvent evaporated, resulting in a pale, green solid. Recrystallization from hot ethyl acetate yielded 4.32 g of a white solid, 1-(11,12-dihydroxydodecyl)-3,7-dimethylxanthine (84% yield).

Workup

  1. customthe resulting reaction mixture
  2. stirringstirred for 1 hour
  3. extractionThe reaction mixture was extracted with dichloromethane (3×100 ml)
  4. customdried
  5. customthe solvent evaporated
  6. customresulting in a pale, green solid
  7. customRecrystallization from hot ethyl acetate

Sources & evidence

ORD record
ord-e8efce531bbd4701ae8c21c1bd8796e2
Source dataset
uspto-grants-1998_06
Patent number
US05770595

Reaction notes

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