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

HRID 1421234Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1421234
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]

Komponenten

5

Edukt 1

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

Produkt 1

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

Reagenzien, Katalysatoren, Lösungsmittel 3

HCID 23938PalladiumKatalysatorHCID 176Acetic AcidLösungsmittelHCID 8857Ethyl AcetateLösungsmittel

Versuchsvorschrift

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.

Aufarbeitung

  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

Quellen und Nachweise

ORD-Eintrag
ord-cdbf8b9e8e2549128cd734aeea957ba9
Quelldatensatz
uspto-grants-2000_06
Patentnummer
US06075029

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