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

HRID 1421233Notes

Reaction equation

HRID 1421233 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>[CH2:21]([N:17]1[C:18]2[C:19](=[O:20])[N:10]([CH2:9][CH2:8][CH2:7][CH2:6][C@H:5]([OH:4])[CH3:30])[C:11](=[O:12])[N:13]([CH3:29])[C:14]=2[N:15]=[C:16]1[CH3:28])[C:22]1[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=1

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-dimethylxanthine

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 treated with 1 M hydrochloric acid in ether (2.5 ml) and stirred for 12 hours. After evaporation of volatiles under reduced pressure, the residue was dissolved in ethyl acetate (100 ml), washed with saturated sodium bicarbonate solution (30 ml), dried over anhydrous magnesium sulfate and concentrated. Yield=420 mg.

Workup

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

Sources & evidence

ORD record
ord-efdcae532746460db38be00403aaf118
Source dataset
uspto-grants-2000_06
Patent number
US06075029

Reaction notes

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