[CH:1](NC(C)C)(C)C.[Li]CCCC.[CH2:13]([O:15][C:16]([CH:18]1[CH2:23][CH2:22][CH2:21][CH2:20][N:19]1[C:24](=[O:31])[C:25]1[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=1)=[O:17])[CH3:14].CI>C1COCC1>[CH2:13]([O:15][C:16]([C:18]1([CH3:1])[CH2:23][CH2:22][CH2:21][CH2:20][N:19]1[C:24](=[O:31])[C:25]1[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=1)=[O:17])[CH3:14]To a solution of diisopropyl amine (2.11 g, 25.86 mmol) in THF (50 mL) at 0° C. was added nBuLi (9.4 mL, 23.51 mmol, 2.5M in hexanes). This solution was stirred for 15 min at 0° C. and then cooled to -78° C. Ethyl-1-benzoyl-piperidine-2-carboxylate (6.16 g, 23.5 mmol) was added and the reaction was allowed to stir for 45 min at which time methyl iodide (3.34 g, 23.51 mmol) was added. The reaction was warmed to room temperature and gently warmed (~40° C.) for 2 h. The reaction was quenched with NaHCO3, extracted with ether, dried over Na2SO4 and concentrated to give ethyl-1-benzoyl-2-methyl-piperidine-2-carboxylate (6.49 g, 100% yield). 1H NMR (300 MHz, CDCl3) δ1.10 (m, 3H), 1.45 (s, 3H), 1.4-1.7 (comp m, 4H), 2.90 (m, 2H), 3.5 (m, 2H), 4.14 (m, 2H), 7.24 (m, 5H).
Loading…
