Potassium Carbonate → (R)-7-benzyl-1-(5-hydroxyhexyl)-3-methylxanthine

HRID 1814973Notes

Reaction equation

HRID 1814973 reaction equation
C(=O)([O-])[O-].[K+].[K+].C([O:10][C@H:11]([CH3:35])[CH2:12][CH2:13][CH2:14][CH2:15][N:16]1[C:25](=[O:26])[C:24]2[N:23]([CH2:27][C:28]3[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=3)[CH:22]=[N:21][C:20]=2[N:19]([CH3:34])[C:17]1=[O:18])(=O)C>CO>[CH2:27]([N:23]1[C:24]2[C:25](=[O:26])[N:16]([CH2:15][CH2:14][CH2:13][CH2:12][C@H:11]([OH:10])[CH3:35])[C:17](=[O:18])[N:19]([CH3:34])[C:20]=2[N:21]=[CH:22]1)[C:28]1[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=1

Participants

4

Reactant 2

HCID 11430Potassium CarbonateHCID 53701360(R)-1-(5-acetoxyhexyl)-7-benzyl-3-methylxanthine

Product 1

HCID 9885048(R)-7-benzyl-1-(5-hydroxyhexyl)-3-methylxanthineYield 89.4%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

Potassium carbonate (30 g) was added to a solution of (R)-1-(5-acetoxyhexyl)-7-benzyl-3-methylxanthine (33.7 g, 84.7 mmol) in methanol (400 ml) and refluxed for 12 hours. After concentration under reduced pressure, the residue was partitioned between ethyl acetate (500 ml) and water (300 ml). The organic layer was washed with water (100 ml), dried over anhydrous magnesium sulfate, and concentrated under reduced pressure to provide (R)-7-benzyl-1-(5-hydroxyhexyl)-3-methylxanthine (27 g).

Workup

  1. temperaturerefluxed for 12 hours
  2. concentrationAfter concentration under reduced pressure
  3. customthe residue was partitioned between ethyl acetate (500 ml) and water (300 ml)
  4. washThe organic layer was washed with water (100 ml)
  5. dry with materialdried over anhydrous magnesium sulfate
  6. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-8b2bf3faad0e4bc2877b4fa73320d979
Source dataset
uspto-grants-2005_04
Patent number
US06878715B1

Reaction notes

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