[OH:1][CH:2]1[CH2:7][CH2:6][NH:5][CH2:4][CH2:3]1.[CH:8]1([C:11]([CH:13](Br)[C:14]2[CH:19]=[CH:18][CH:17]=[CH:16][C:15]=2[F:20])=[O:12])[CH2:10][CH2:9]1.C(=O)([O-])[O-].[K+].[K+].O>CN(C)C=O>[CH:8]1([C:11]([CH:13]([N:5]2[CH2:6][CH2:7][CH:2]([OH:1])[CH2:3][CH2:4]2)[C:14]2[CH:19]=[CH:18][CH:17]=[CH:16][C:15]=2[F:20])=[O:12])[CH2:10][CH2:9]13.13 g (31 mmol) of 4-hydroxypiperidine were dissolved in 30 ml of dimethylformamide (DMF), followed by the addition of 7.94 g (31 mmol) of α-cyclopropylcarbonyl-2-fluorobenzyl bromide and 4.7 g (34 mmol) of potassium carbonate. The resulting mixture was stirred at room temperature for 2 hours. Water was added to the reaction mixture and the resulting mixture was extracted with toluene. The organic layer thus obtained was dried over anhydrous sodium sulfate. The solvent was concentrated under reduced pressure. The resulting residue was purified by chromatography on a silica gel column (eluting solvent: chloroform/methanol=19/1), whereby 8.00 g of the title compound were obtained as a brown oil (yield: 93%).
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