Reaction Steps
The 10-methylimino-1,2,3,5,10,10a-hexahydropyrrolo[1,2-b]isoquinolin-3-one (880 mg, 4.1 mmol) was dissolved in THF (12 mL) and added dropwise to a suspension of LAH (623 mg, 16.4 mmol) in THF (12 ml) at room temperature under nitrogen. The suspension was stirred at reflux for 15 hours, cooled, and quenched by the addition of H2O(0.88 mL), NaOH (1.5 N, 0.88 mL) and additional H2O(2.6 mL). The mixture was filtered and the filtrate was concentrated in vacuo to give cis-10-methylamino-1,2,3,5,10,10a-hexahydropyrrolo[1,2-b]isoquinoline as a dark oil (600 mg). Chromatography on silica gel with CH2Cl2/MeOH/NH4OH (95:4:1) provided the product as a dark red, viscous oil (547 mg). 1H NMR (CDCl3, 300 MHz): δ 7.52 (d, J=7.63 Hz, 1H), 7.25 (t, J=7.23, 14.47 Hz, 1H), 7.17 (t, J=7.76, 15.13 Hz, 1H), 7.09 (d, J=7.63 Hz, 1H), 4.03 (d, J=14.01 Hz, 1H), 3.79 (d, J=10.01 Hz, 1H), 3.62 (d, J=14.01 Hz, 1H), 3.17 (m, 1H), 2.58 (m, 1H), 2.47 (m, 1H), 2.41 (s, 3H), 2.28 (m, 1H), 1.87 (m, 1H0, 1.69 (m, 1H); 13C NMR (CDCl3): δ 137.24, 135.83, 126.63, 126.20 (2C), 64.92, 62.70, 55.85, 54.71, 32.33, 30.04, 21.57; IR (neat): 3285 (br), 3060, 3020, 2950, 2870, 2795, 1735-1565 (br), 1475, 1450, 1155, 1035, 920, 905, 780, 720 cm−1; MS (FAB): m/e 203 (M+H, 74.8%), 201 (74.1%), 172 (M−NHMe, 100%), 170 (85%), 133 (53.1%), 132 (27%), 118 (17.7%); HRMS (FAB): Calc for C13H18N2 202.1469, found 203.1555 (M+H).
