Ethyl 7-(1-(tert-butoxycarbonyl)-1,2,3,6-tetrahydropyridin-4-yl)imidazo[1,2-a]pyridine-3-carboxylate → Ethyl 7-(1-(tert-butoxycarbonyl)piperidin-4-yl)imidazo[1,2-a]pyridine-3-carboxylate
反応式
[C:1]([O:5][C:6]([N:8]1[CH2:13][CH:12]=[C:11]([C:14]2[CH:19]=[CH:18][N:17]3[C:20]([C:23]([O:25][CH2:26][CH3:27])=[O:24])=[CH:21][N:22]=[C:16]3[CH:15]=2)[CH2:10][CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2]>CO.[OH-].[OH-].[Pd+2]>[C:1]([O:5][C:6]([N:8]1[CH2:13][CH2:12][CH:11]([C:14]2[CH:19]=[CH:18][N:17]3[C:20]([C:23]([O:25][CH2:26][CH3:27])=[O:24])=[CH:21][N:22]=[C:16]3[CH:15]=2)[CH2:10][CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2]参加物
4
実験手順
H2(balloon) was introduced to a stirred mixture of Pd(OH)2/C (0.055 g) and ethyl 7-(1-(tert-butoxycarbonyl)-1,2,3,6-tetrahydropyridin-4-yl)imidazo[1,2-a]pyridine-3-carboxylate (89) (0.55 g, 1.48 mmol) in MeOH (5 mL). After 6 hours, the mixture was filtered through a pad of Celite and the solvent was evaporated to give the crude product. The residue was purified over silica using EtOAc and hexanes to give ethyl 7-(1-(tert-butoxycarbonyl)piperidin-4-yl)imidazo[1,2-a]pyridine-3-carboxylate (90). 1H NMR (400 MHz, CD2Cl2) δ 9.27 (d, J=7.2 Hz, 1H), 8.27 (s, 1H), 7.64 (s, 1H), 7.04 (dd, J=1.6, 7.2 Hz, 1H), 4.43 (q, J=7.2 Hz, 2H), 4.31 (m, 2H), 2.87 (m, 1H), 2.83 (m, 2H), 1.95 (m, 2H), 1.67 (m, 2H), 1.49 (s, 9H), 1.43 (t, J=7.2 Hz, 3H). MS m/z 374.2 (M+1)+.