Water → 1-(8,9-Dihydroxynonyl)-3,7-dimethylxanthine

HRID 1289925Notes

Reaction equation

HRID 1289925 reaction equation
[CH2:1]([N:10]1[C:19](=[O:20])[C:18]2[N:17]([CH3:21])[CH:16]=[N:15][C:14]=2[N:13]([CH3:22])[C:11]1=[O:12])[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH:8]=[CH2:9].C[N+]1([O-])CC[O:27]CC1.[OH2:31].S(S([O-])=O)([O-])=O.[Na+].[Na+]>C(O)(C)(C)C.CC(C)=O.[Os](=O)(=O)(=O)=O>[OH:31][CH:8]([CH2:9][OH:27])[CH2:7][CH2:6][CH2:5][CH2:4][CH2:3][CH2:2][CH2:1][N:10]1[C:19](=[O:20])[C:18]2[N:17]([CH3:21])[CH:16]=[N:15][C:14]=2[N:13]([CH3:22])[C:11]1=[O:12]

Participants

8

Reactant 4

HCID 962WaterHCID 24489Sodium DithioniteHCID 82029Methyl morpholine oxideHCID 152306351-(8-Nonenyl)-3,7-dimethylxanthine

Product 1

HCID 98408081-(8,9-Dihydroxynonyl)-3,7-dimethylxanthineYield 54%

Reagents, catalysts & solvents 3

HCID 6386tert-ButanolCatalystHCID 30318Osmium TetroxideCatalystHCID 180AcetoneSolvent

Procedure

A solution of 1-(8-nonenyl)-3,7-dimethylxanthine (810 mg, 2.7 mmol), 4-methylmorpholine-N-oxide (340 mg, 2.9 mmol) and 2.5% osmium tetroxide in t-butanol (3 drops) in acetone (20 ml) and water (20 ml) was stirred for 24 hours. Saturated aqueous sodium dithionite solution (5 ml) was added. After stirring for 15 minutes, the reaction was extracted with 25% ethanol-dichloromethane (4×50 ml). The combined organic phases were dried over sodium sulfate and the solvents evaporated under vacuum. The solid residue was recrystallized (ethanol-chloroform) to give 1-(8,9-dihydroxynonyl)-3,7-dimethylxanthine (490 mg, 54% yield).

Workup

  1. extractionthe reaction was extracted with 25% ethanol-dichloromethane (4×50 ml)
  2. dry with materialThe combined organic phases were dried over sodium sulfate
  3. customthe solvents evaporated under vacuum
  4. customThe solid residue was recrystallized (ethanol-chloroform)

Sources & evidence

ORD record
ord-757896fa3136447782d6737b3f27954c
Source dataset
uspto-grants-1998_05
Patent number
US05750575

Reaction notes

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