3-(benzyloxy)-5-(biphenyl-3-yl)-6-(1-hydroxy-2-phenylethyl)-1-methylpyridin-2(1H)-one → 5-(biphenyl-3-yl)-3-hydroxy-6-(1-hydroxy-2-phenylethyl)-1-methylpyridin-2(1H)-one
Reaktionsgleichung
C([O:8][C:9]1[C:10](=[O:37])[N:11]([CH3:36])[C:12]([CH:27]([OH:35])[CH2:28][C:29]2[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=2)=[C:13]([C:15]2[CH:16]=[C:17]([C:21]3[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=3)[CH:18]=[CH:19][CH:20]=2)[CH:14]=1)C1C=CC=CC=1>CO.[Pd]>[C:17]1([C:21]2[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=2)[CH:18]=[CH:19][CH:20]=[C:15]([C:13]2[CH:14]=[C:9]([OH:8])[C:10](=[O:37])[N:11]([CH3:36])[C:12]=2[CH:27]([OH:35])[CH2:28][C:29]2[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=2)[CH:16]=1Komponenten
4
Edukt 1
Produkt 1
Reagenzien, Katalysatoren, Lösungsmittel 2
Versuchsvorschrift
To a solution of 3-(benzyloxy)-5-(biphenyl-3-yl)-6-(1-hydroxy-2-phenylethyl)-1-methylpyridin-2(1H)-one (100 mg, 0.205 mmol) in 5 mL methanol, was added 10% palladium on charcoal (21.83 mg, 0.02 mmol). The resulting mixture was stirred at room temperature under hydrogen (1 atm) for 45 min. The mixture was filtered to remove charcoal, concentrated and purified by reversed-phase HPLC to afford 5-(biphenyl-3-yl)-3-hydroxy-6-(1-hydroxy-2-phenylethyl)-1-methylpyridin-2(1H)-one (25.4 mg, 0.064 mmol, 31.2% yield). ES-MS (M+H)+=398. High resolution mass spec (ESI) calc (M+H)+=398.1751 found 398.1754