HCID 15521821, Verbindung → trans-10-Methylamino-1,2,3,5,10,10a-hexahydropyrrolo[1,2-b]isoquinolin-3-one
Reaktionsgleichung
[CH3:1][N:2]=[C:3]1[C:12]2[CH:11]=[CH:10][CH:9]=[CH:8][C:7]=2[CH2:6][N:5]2[C:13](=[O:16])[CH2:14][CH2:15][CH:4]12>CCO.[Pd]>[CH3:1][NH:2][C@@H:3]1[C:12]2[CH:11]=[CH:10][CH:9]=[CH:8][C:7]=2[CH2:6][N:5]2[C:13](=[O:16])[CH2:14][CH2:15][C@H:4]12Komponenten
4
Edukt 1
Produkt 1
Reagenzien, Katalysatoren, Lösungsmittel 2
Versuchsvorschrift
A mixture of 10methylimino-1,2,3,5,10,10a-hexahydropyrrolo[1,2-b]isoquinolin-3-one (159 mg) and Pd/C (10%, 110 mg) in EtOH (10 mL) was hydrogenated in a shaker apparatus at 50 psi overnight, and then filtered. The filtrate was concentrated in vacuo and the residue was chromatographed on silica gel eluting with CH2Cl2/MeOH/NH4OH (150/8/1) to give an oil (11 mg): 1H NMR (300 MHz) δ 7.25 (m, 4 H), 4.92 (d, J=18.0 Hz, 1 H), 4.31 (d, J=17.7 Hz, 1 H), 3.95 (m, 1 H), 3.43 (d, J=2.7 Hz, 1 H), 2.38 (s, NCH3); MS (FAB), m/e 217 (100, M+H), 154 (55), 136 (45).