Reaktionsgleichung
FC(F)(F)C(O)=O.[CH2:8]([O:15][C:16]([N:18]1[CH2:23][CH2:22][CH:21]([C:24]2(O)[CH:33]([C:34]3[CH:39]=[CH:38][CH:37]=[CH:36][CH:35]=3)[C:32]3[C:27](=[CH:28][CH:29]=[C:30]([O:40][CH3:41])[CH:31]=3)[C:26](=[O:42])[N:25]2[CH3:43])[CH2:20][CH2:19]1)=[O:17])[C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=1.[OH-].[Na+]>>[CH2:8]([O:15][C:16]([N:18]1[CH2:19][CH2:20][CH:21]([C:24]2[N:25]([CH3:43])[C:26](=[O:42])[C:27]3[C:32]([C:33]=2[C:34]2[CH:39]=[CH:38][CH:37]=[CH:36][CH:35]=2)=[CH:31][C:30]([O:40][CH3:41])=[CH:29][CH:28]=3)[CH2:22][CH2:23]1)=[O:17])[C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=1Komponenten
4
Versuchsvorschrift
To trifluoroacetic acid (1 mL) at room temperature was added benzyl-4-(3-hydroxy-6-methoxy-2-methyl-1-oxo-4-phenyl-1,2,3,4-tetra-hydroisoquinolin-3-yl)piperidine-1-carboxylate (215 mg, 0.443 mmol) with stirring. After 10 min. the reaction mixture was made basic with 2N sodium hydroxide, extracted with methylene chloride (3×) and dried with anhydrous sodium sulfate. Filtration followed by evaporation of solvent in vacuo gave a solid which was triturated with hexane-ethyl acetate to afford benzyl-4-(6-methoxy-2-methyl-1-oxo-4-phenyl-1,2-dihydroisoquinolin-3-yl)piperidine-1-carboxylate as a solid (141 mg, 0.292 mmol, 66%). MS [M+H]+ 483.2
Aufarbeitung
- extractionextracted with methylene chloride (3×)
- dry with materialdried with anhydrous sodium sulfate
- filtrationFiltration
- customfollowed by evaporation of solvent in vacuo
- customgave a solid which
- customwas triturated with hexane-ethyl acetate
Quellen und Nachweise
- ORD-Eintrag
- ord-f659c169bffc48da81ef2f18e143341e
- Quelldatensatz
- uspto-grants-2010_06
- Patentnummer
- US07741322B2
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