Hydrochloric Acid → (S)-1-(5-hydroxyhexyl)-7-benzyl-3-methylxanthine

HRID 1835735Notes

Reaction equation

HRID 1835735 reaction equation
C([O:4][C@@H:5]([CH3:29])[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)[CH:16]=[N:15][C:14]=2[N:13]([CH3:28])[C:11]1=[O:12])(=O)C.Cl>CO.CCOCC>[OH:4][C@@H:5]([CH3:29])[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)[CH:16]=[N:15][C:14]=2[N:13]([CH3:28])[C:11]1=[O:12]

Participants

5

Reactant 2

HCID 313Hydrochloric AcidHCID 53701359(S)-1-(5-acetoxyhexyl)-7-benzyl-3-methylxanthine

Product 1

HCID 11610099(S)-1-(5-hydroxyhexyl)-7-benzyl-3-methylxanthineYield 86.2%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 3283Diethyl EtherSolvent

Procedure

A solution of (S)-1-(5-acetoxyhexyl)-7-benzyl-3-methylxanthine (350 mg) in methanol (10 ml) was treated with 1 M hydrogen chloride in ether (5 ml). After stirring at room temperature for 12 hours, the solvent was evaporated under reduced pressure. The residue was dissolved in dichloromethane (100 ml). The solution was washed with saturated aqueous sodium bicarbonate solution (30 ml), dried over anhydrous magnesium sulfate and concentrated under reduced pressure to give (S)-1-(5-hydroxyhexyl)-7-benzyl-3-methylxanthine (270 mg).

Workup

  1. customthe solvent was evaporated under reduced pressure
  2. dissolutionThe residue was dissolved in dichloromethane (100 ml)
  3. washThe solution was washed with saturated aqueous sodium bicarbonate solution (30 ml)
  4. dry with materialdried over anhydrous magnesium sulfate
  5. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-3d576104ca0d4f7c80dd80563d5514eb
Source dataset
uspto-grants-2004_08
Patent number
US06774130B2

Reaction notes

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