[CH:1]1[CH:6]=[CH:5][C:4]([CH2:7][O:8][C:9](Cl)=[O:10])=[CH:3][CH:2]=1.[NH:12]1[CH2:17][CH2:16][CH:15]([CH2:18][C:19]([O:21][CH2:22][CH3:23])=[O:20])[CH2:14][CH2:13]1.C(=O)([O-])[O-].[Na+].[Na+]>ClCCl>[CH2:22]([O:21][C:19](=[O:20])[CH2:18][CH:15]1[CH2:16][CH2:17][N:12]([C:9]([O:8][CH2:7][C:4]2[CH:5]=[CH:6][CH:1]=[CH:2][CH:3]=2)=[O:10])[CH2:13][CH2:14]1)[CH3:23]Benzyl chloridocarbonate (10.5 g, 61.3 mmol) was added to a solution of ethyl piperidin-4-ylacetate (10.0 g, 58.4 mmol) and sodium carbonate (46.2 g, 438 mmol) in dichloromethane (320 mL). After 18 h, the reaction mixture was filtered and concentrated. Purification by silica gel chromatography [75% hexanes/ethyl acetate→50% hexanes/ethyl acetate)] gave the title compound (17.6 g). MS 306.1 (M+1).
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