[CH3:1][O:2][C:3]1[CH:8]=[CH:7][C:6]([C:9]([CH:11]2[CH2:16][CH2:15][NH:14][CH2:13][CH2:12]2)=[O:10])=[CH:5][CH:4]=1.C(N(CC)CC)C.Br[CH2:25][C:26]([O:28][CH2:29][CH3:30])=[O:27]>C(#N)C.C([O-])(O)=O.[Na+]>[CH2:29]([O:28][C:26](=[O:27])[CH2:25][N:14]1[CH2:15][CH2:16][CH:11]([C:9](=[O:10])[C:6]2[CH:5]=[CH:4][C:3]([O:2][CH3:1])=[CH:8][CH:7]=2)[CH2:12][CH2:13]1)[CH3:30]To a solution of 4-methoxy-phenyl-piperidin-4-yl-methanone (20 g, 78 mmol, 1 eq.) in 313 mL of acetonitrile was added triethylamine (22 mL, 156 mmol, 2 eq.), followed by ethyl 2-bromoacetate (9.5 mL, 86 mmol, 1.1 eq.) dropwise. The resulting mixture was heated at 85° C. overnight. After 18 h, the reaction mixture was diluted with saturated NaHCO3 (150 mL) and extracted with ethyl acetate (3×500 mL). The combined organic layers were washed with brine, dried over anhydrous Na2SO4, filtered, and concentrated in vacuo to give an oil. This oil was purified by silica gel column chromatography (10-20% acetone/heptane) to give the title compound as a white solid (11.7 g, 49% yield). Exact mass calculated for C17H24N1O4 306.2. MS (ESI) m/z 306.4 (M+H)+.
読み込み中…
