8-benzyloxy-5-{1-hydroxy-2-[1-(4-trifluoromethyl-benzyl)-cyclopropylamino]-ethyl}-1H-quinolin-2-one → 8-hydroxy-5-{1-hydroxy-2-[1-(4-trifluoromethyl-benzyl)-cyclopropylamino]-ethyl}-1H-quinolin-2-one
Reaktionsgleichung
C([O:8][C:9]1[CH:10]=[CH:11][C:12]([CH:20]([OH:37])[CH2:21][NH:22][C:23]2([CH2:26][C:27]3[CH:32]=[CH:31][C:30]([C:33]([F:36])([F:35])[F:34])=[CH:29][CH:28]=3)[CH2:25][CH2:24]2)=[C:13]2[C:18]=1[NH:17][C:16](=[O:19])[CH:15]=[CH:14]2)C1C=CC=CC=1>CO.[Pd]>[OH:8][C:9]1[CH:10]=[CH:11][C:12]([CH:20]([OH:37])[CH2:21][NH:22][C:23]2([CH2:26][C:27]3[CH:28]=[CH:29][C:30]([C:33]([F:36])([F:34])[F:35])=[CH:31][CH:32]=3)[CH2:25][CH2:24]2)=[C:13]2[C:18]=1[NH:17][C:16](=[O:19])[CH:15]=[CH:14]2Komponenten
4
Edukt 1
Produkt 1
Reagenzien, Katalysatoren, Lösungsmittel 2
Versuchsvorschrift
322 mg (0.63 mmol) 8-benzyloxy-5-{1-hydroxy-2-[1-(4-trifluoromethyl-benzyl)-cyclopropylamino]-ethyl}-1H-quinolin-2-one are dissolved in 10 mL methanol and hydrogenated in the presence of palladium on charcoal at 3 bar. The precipitated product is dissolved by adding methanol. The catalyst is separated off and the filtrate is evaporated down. The precipitated solid is filtered off and suspended in diethyl ether for further purification. Yield: 161 mg (61%); mass spectroscopy: [M+H]+=419.
Aufarbeitung
- dissolutionThe precipitated product is dissolved
- customThe catalyst is separated off
- customthe filtrate is evaporated down
- filtrationThe precipitated solid is filtered off
- customsuspended in diethyl ether for further purification
Quellen und Nachweise
- ORD-Eintrag
- ord-798c6c29c88e4d63a10061c1068dcda1
- Quelldatensatz
- uspto-grants-2009_07
- Patentnummer
- US07563806B2
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