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

HRID 1421234Notes

Reaction equation

HRID 1421234 reaction equation
C([N:8]1[C:16]2[C:15](=[O:17])[N:14]([CH2:18][CH2:19][CH2:20][CH2:21][C@H:22]([OH:24])[CH3:23])[C:13](=[O:25])[N:12]([CH3:26])[C:11]=2[N:10]=[C:9]1[CH3:27])C1C=CC=CC=1>C(O)(=O)C.C(OCC)(=O)C.[Pd]>[OH:24][C@H:22]([CH3:23])[CH2:21][CH2:20][CH2:19][CH2:18][N:14]1[C:15](=[O:17])[C:16]2[NH:8][C:9]([CH3:27])=[N:10][C:11]=2[N:12]([CH3:26])[C:13]1=[O:25]

Participants

5

Reactant 1

HCID 9929299(R)-1-(5-hydroxyhexyl)-7-benzyl-3,8-dimethylxanthine

Product 1

HCID 9860506(R)-1-(5-Hydroxyhexyl)-3,8-dimethylxanthine

Reagents, catalysts & solvents 3

HCID 23938PalladiumCatalystHCID 176Acetic AcidSolventHCID 8857Ethyl AcetateSolvent

Procedure

A solution of (R)-7-benzyl-1-(5-hydroxyhexyl)-3,8-dimethylxanthine (250 mg) in a mixture of acetic acid (10 ml) and ethyl acetate (10 ml) was hydrogenated in presence of palladium on carbon (50 mg) for 12 hours. The mixture was filtered through celite (5 g) and concentrated. The residue was dissolved in ethyl acetate (100 ml), washed with saturated sodium bicarbonate solution (50 ml), dried over magnesium sulfate and concentrated. The product was purified by flash chromatography (silica gel) eluting with 10% methanol/ethyl acetate. Yield=180 mg.

Workup

  1. filtrationThe mixture was filtered through celite (5 g)
  2. concentrationconcentrated
  3. dissolutionThe residue was dissolved in ethyl acetate (100 ml)
  4. washwashed with saturated sodium bicarbonate solution (50 ml)
  5. dry with materialdried over magnesium sulfate
  6. concentrationconcentrated
  7. customThe product was purified by flash chromatography (silica gel)
  8. washeluting with 10% methanol/ethyl acetate

Sources & evidence

ORD record
ord-cdbf8b9e8e2549128cd734aeea957ba9
Source dataset
uspto-grants-2000_06
Patent number
US06075029

Reaction notes

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