反应详情

To a stirred solution of (3S,4S)-4-(aminomethyl)-1-{2-[6-(methyloxy)-1,5-naphthyridin-4-yl]ethyl}-3-pyrrolidinol (0.30 g, 1.0 mmole) in dry CH2Cl2 (25 mL) and dry EtOH (10 mL) at RT was added 2,3-dihydro[1,4]dioxino[2,3-c]pyridine-7-carbaldehyde (0.165 g, 1.0 mmole). After 24 h, at RT was added NaBH(OAc)3 (0.32 g, 1.5 mmole). After 2 h, the reaction solution was concentrated under vacuum and purified on silica (CHCl3/MeOH, 9:1 containing 5% NH4OH) to afford the title compound (0.12 g, 27%) as light yellow solid: 1H NMR (400 MHz, CD3OD) δ 8.67 (d, J=4.5 Hz, 1H), 8.19 (d, J=9.0 Hz, 1H), 7.68 (d, J=4.5 Hz, 1H), 7.25 (d, J=9.0 Hz, 1H), 7.02 (s, 1H), 4.61 (m, 1H), 4.38 (m, 4H), 4.20 (s, 2H), 4.15 (s, 3H), 3.60 (m, 8H), 3.42 (m, 1H), 3.25 (m, 1H), 2.82 (m, 1H). LC-MS (ES) m/e 452 (M+H)+.

1. waitAfter 2 h
2. concentrationthe reaction solution was concentrated under vacuum
3. custompurified on silica (CHCl3/MeOH, 9:1 containing 5% NH4OH)