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

HRID 1954106Notes

Reaction equation

HRID 1954106 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>[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

7

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 2

HCID 6386tert-ButanolCatalystHCID 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% oxmium 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 portions were dried over sodium sulfate, and the solvents were evaporated under vacuum. The solid residue was recrystallized (ethanol-chloroform), yielding 490 mg (54%) 1-(8,9-dihydroxynonyl)-3,7-dimethylxanthine (inventive compound no. 1561).

Workup

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

Sources & evidence

ORD record
ord-210a0031f0ae4f4ab9bedb724b6416dd
Source dataset
uspto-grants-2000_09
Patent number
US06121270

Reaction notes

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