Reaktion #46150

Reaktionsgleichung

trifluoroacetic acid

benzyl-4-(3-hydroxy-6-methoxy-2-methyl-1-oxo-4-phenyl-1,2,3,4-tetra-hydroisoquinolin-3-yl)piperidine-1-carboxylate

sodium hydroxide

→

benzyl-4-(6-methoxy-2-methyl-1-oxo-4-phenyl-1,2-dihydroisoquinolin-3-yl)piperidine-1-carboxylate

Ausbeute 66.0%

Reaktionsbedingungen

Aufarbeitung

1. 1
   Extraktionextracted with methylene chloride (3×)
2. 2
   Trocknendried with anhydrous sodium sulfate
3. 3
   FiltrationFiltration
4. 4
   Sonstigefollowed by evaporation of solvent in vacuo
5. 5
   Sonstigegave a solid which
6. 6
   Sonstigewas triturated with hexane-ethyl acetate

Vorschrift

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

Quelle