[H-].[Na+].C(O)C.[C:6]([CH:11]1[CH2:16][CH2:15][CH2:14][NH:13][C:12]1=[O:17])([O:8][CH2:9][CH3:10])=[O:7].[N+:18]([C:21]1[CH:28]=[CH:27][CH:26]=[CH:25][C:22]=1[CH2:23]Br)([O-:20])=[O:19]>O>[N+:18]([C:21]1[CH:28]=[CH:27][CH:26]=[CH:25][C:22]=1[CH2:23][C:11]1([C:6]([O:8][CH2:9][CH3:10])=[O:7])[CH2:16][CH2:15][CH2:14][NH:13][C:12]1=[O:17])([O-:20])=[O:19]Sodium hydride (60% dispersion in oil, 2.45 g) was added to ethanol (100 ml), to which was added 3-carboethoxy-2-piperidone (10.0 g). The reaction mixture was stirred for 15 minutes, to which was added 2-nitrobenzyl bromide (13.2 g) at room temperature. The reaction mixture was stirred at 60° C. for 3 hours. Water was added to the reaction mixture, which was concentrated. The residue was diluted with water and extracted with ethyl acetate. The organic layer was washed with water and a saturated aqueous sodium chloride solution, then dried and concentrated. The obtained crude crystals were recrystallized from ethyl acetate-hexane to give the entitled compound (14.6 g).
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