Reaction Steps
4-((9aS)-3-(Ethoxycarbonyl)-5-oxo-2-{2-[4-(trifluoromethyl)phenyl]ethyl}-7,8,9,9a-tetrahydro-5H-pyrido[2,3-α]pyrrolizin-4-yl)benzoic acid (0.178 g, 0.331 mmol) was dissolved in 4 mL DCM. (1R)-1-(4-Pyridinyl)ethylamine (0.081 g, 0.661 mmol) was added followed by HOBT (0.054 g, 0.397 mmol) and EDC (0.076 mg, 0.397 mmol). After 3 h, the reaction mixture was washed with pH 4.0 phosphate buffer (2×), 5% NaHCO3, and brine and dried over MgSO4. Purification on SiO2 (EtOAc 100% to EtOAc:MeOH:NH4OH 95:5:0.3) then by TLC (SiO2; EtOAc:MeOH 95:5) provided the title compound as a tan solid (0.077 g, 0.12 mmol, 36%): 1H NMR (400 MHz, CDCl3) δ 8.52 (d, J=6.0 Hz, 2H), 7.80 (d, J=8.0 Hz, 2H), 7.51 (d, J=8.0 Hz, 2H), 7.42 (d, J=8.4 Hz, 2H), 7.30 (d, J=8.4 Hz, 2H), 7.27 (d, J=4.4 Hz, 2H), 6.51 (d, J=7.2 Hz, 1H), 5.27 (m, 1H), 4.69 (dd, J=10.4, 6.4 Hz, 1H), 3.99 (m, 2H), 3.66 (m, 1H), 3.35 (m, 1H), 3.18 (m, 2H), 3.14 (m, 1H), 2.45 (m, 1H), 2.33 (m, 2H), 1.7 (bs, 1NH, 2H2O), 1.56 (d, J=6.8 Hz, 3H), 1.35 (m, 1H), 0.91 (t, J=6.8 Hz, 3H) ppm. ESMS m/z (pos. ion) 643 (M+H)+, (neg. ion) 641 (M−H)+.
