Hydrochloric Acid → (R)-1-(5-hydroxyhexyl)-7-benzyl-3,8-dimethylxanthine

HRID 1835705Notes

Reaction equation

HRID 1835705 reaction equation
C([O:4][C@H:5]([CH3:30])[CH2:6][CH2:7][CH2:8][CH2:9][N:10]1[C:19](=[O:20])[C:18]2[N:17]([CH2:21][C:22]3[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=3)[C:16]([CH3:28])=[N:15][C:14]=2[N:13]([CH3:29])[C:11]1=[O:12])(=O)C.Cl>CO.CCOCC>[OH:4][C@H:5]([CH3:30])[CH2:6][CH2:7][CH2:8][CH2:9][N:10]1[C:19](=[O:20])[C:18]2[N:17]([CH2:21][C:22]3[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=3)[C:16]([CH3:28])=[N:15][C:14]=2[N:13]([CH3:29])[C:11]1=[O:12]

Participants

5

Reactant 2

HCID 313Hydrochloric AcidHCID 54438002(R)-1-(5-acetoxyhexyl)-7-benzyl-3,8-dimethylxanthine

Product 1

HCID 9929299(R)-1-(5-hydroxyhexyl)-7-benzyl-3,8-dimethylxanthineYield 93.5%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 3283Diethyl EtherSolvent

Procedure

A solution of (R)-1-(5-Acetoxyhexyl)-7-benzyl-3,8-dimethylxanthine (500 mg) in methanol (20 ml) was combined with hydrogen chloride in ether (1 M, 2.5 ml) and stirred at room temperature for 12 hours. After evaporation of the solvent under reduced pressure, the residue was dissolved in ethyl acetate (100 ml). The solution was washed with saturated aqueous sodium bicarbonate solution (30 ml), dried over magnesium sulfate and concentrated under reduced pressure to provide (R)-1-(5-hydroxyhexyl)-7-benzyl-3,8-dimethylxanthine (420 mg).

Workup

  1. customAfter evaporation of the solvent under reduced pressure
  2. dissolutionthe residue was dissolved in ethyl acetate (100 ml)
  3. washThe solution was washed with saturated aqueous sodium bicarbonate solution (30 ml)
  4. dry with materialdried over magnesium sulfate
  5. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-75346bbf2d79477e90ad9e5f2748d54e
Source dataset
uspto-grants-2004_08
Patent number
US06774130B2

Reaction notes

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