Reaction Steps
NaBII4 (0.226 g, 5.97 mmol) is added in portions to a mixture of 9 (1.17 g, 3.98 mmol) and (S)-4-(4-(1-aminoethyl)phenyl)-1-methylpyridin-2(1H)-one (15) (1.00 g, 4.37 g) in MeOH (5 mL). The mixture is stirred at 25° C. for 15 h, then treated with K2CO3 (1.65 g, 11.93 mmol) followed by phenyl chloroformate (0.93, 5.97 mmol). The resultant suspension is then stirred at 25° C. for 1 hour, treated with water (15 mL) over 30 min, and stirred at 25° C. for 2 hours. The solids are collected by filtration, rinsed with MeOH/water (⅓, 20 mL), and dried to provide 14 as off-white solid. Yield: 1.76 g, 79.8%. 1H NMR (DMSO-d6, 500 MHz): δ 7.77 (d, J=7.2 Hz, 1H), 7.66 (m, 2H), 7.46-7.00 (m, 12H), 6.67 (d, J=2.1 Hz, 1H), 6.56 (dd, J=7.0, 2.1 Hz, 1H), 5.82 (s, 1H), 5.28 (br s, 1H), 5.11 (s, 1H), 3.45 (s, 3H), 3.35 (m, 1H), 2.59 (m, 1H), 2.14-1.81 (m, 4H), 1.55-1.29 (m, 3H), 1.01 (s, 3H), 0.61 (s, 3H); 13C NMR (DMSO-d6, 400 MHz): δ 161.97, 154.08, 151.20, 150.09, 147.53, 142.31, 139.85, 135.59, 129.18, 127.59, 127.40, 126.66, 125.87, 125.35, 125.07, 121.77, 114.79, 103.75, 75.53, 71.48, 53.82, 51.19, 44.90, 36.36, 32.80, 29.22, 21.58, 17.00; LC-MS (ES): m/z 555 (M+H), 479 (100).
