Br[C:2]1[CH:7]=[CH:6][C:5]2[O:8][CH2:9][O:10][C:4]=2[CH:3]=1.CCCCCC.C([Li])CCC.C(OC([N:27]1[CH2:32][CH2:31][C:30](=[O:33])[CH2:29][CH2:28]1)=O)C.O>O1CCCC1>[O:8]1[C:5]2[CH:6]=[CH:7][C:2]([C:30]3([OH:33])[CH2:31][CH2:32][NH:27][CH2:28][CH2:29]3)=[CH:3][C:4]=2[O:10][CH2:9]14-Bromo-1,2-(methylenedioxy)benzene (Tokyo Chemical Industry CO., LTD., 2.0 g) was dissolved in tetrahydrofuran (15 ml) and the mixture was cooled to −78° C. An n-butyllithium hexane solution (2.44 M, 5.7 ml) was added to the solution. The mixture was stirred at −78° C. for 1 hr, and 1-(ethoxycarbonyl)-4-piperidone (Aldrich Co., 1.7 g) was added. Then, the reaction temperature was raised to 0° C., and the mixture was further stirred for 1 hr. After completion of the reaction, water was added and the mixture was extracted three times with ethyl acetate. The organic layer was dried and the solvent was evaporated under reduced pressure. The obtained residue was purified by silica gel column chromatography (elution solvent: hexane-ethyl acetate (5:1-2:1)). Then, the residue was dissolved in ethylene glycol (20 ml), a 50% aqueous potassium hydroxide solution was added, and the mixture was stirred with heating at 120° C. for 6 hr. After completion of the reaction, the mixture was extracted three times with chloroform. The organic layer was dried and the solvent was evaporated under reduced pressure to give 4-(1,3-benzodioxol-5-yl)piperidin-4-ol (1.0 g, yield 43%).
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