(+/-)-alpha-(6-(Benzyloxy)-2-naphthyloxymethyl)-3-pyridinepropanol → alpha-(6-Hydroxy-2-naphthyloxymethyl)-3-pyridinepropanol

HRID 1600907Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1600907
C([O:8][C:9]1[CH:10]=[C:11]2[C:16](=[CH:17][CH:18]=1)[CH:15]=[C:14]([O:19][CH2:20][CH:21]([OH:30])[CH2:22][CH2:23][C:24]1[CH:25]=[N:26][CH:27]=[CH:28][CH:29]=1)[CH:13]=[CH:12]2)C1C=CC=CC=1>C(O)C.[Pd]>[OH:8][C:9]1[CH:10]=[C:11]2[C:16](=[CH:17][CH:18]=1)[CH:15]=[C:14]([O:19][CH2:20][CH:21]([OH:30])[CH2:22][CH2:23][C:24]1[CH:25]=[N:26][CH:27]=[CH:28][CH:29]=1)[CH:13]=[CH:12]2

Komponenten

4

Edukt 1

HCID 21830659(+/-)-alpha-(6-(Benzyloxy)-2-naphthyloxymethyl)-3-pyridinepropanol

Produkt 1

HCID 21830706alpha-(6-Hydroxy-2-naphthyloxymethyl)-3-pyridinepropanolAusbeute 78,9 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 23938PalladiumKatalysatorHCID 702EthanolLösungsmittel

Versuchsvorschrift

Solid α-(6-(benzyloxy)-2-naphthyloxymethyl)-3-pyridinepropanol (0.90 g; from Example 29 above) was dissolved in dry ethanol (20 ml) and hydrogenated for 2 hours at 5 atmospheres pressure using palladium on carbon (10%, 1 spatula end) as catalyst. The reaction was filtered through Celite and the residue washed with ethanol. The combined filtrate and washings were concentrated under reduced pressure and the residue obtained purified by column chromatography over silica eluting with dichloromethane:methanol (95:5) to give a white solid (0.55 g).

Aufarbeitung

  1. filtrationThe reaction was filtered through Celite
  2. washthe residue washed with ethanol
  3. concentrationThe combined filtrate and washings were concentrated under reduced pressure
  4. customthe residue obtained
  5. custompurified by column chromatography over silica eluting with dichloromethane:methanol (95:5)

Quellen und Nachweise

ORD-Eintrag
ord-1765acf5a7df4f019f4e2394c2bab546
Quelldatensatz
uspto-grants-1999_11
Patentnummer
US05977105

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