[H-].[Al+3].[Li+].[H-].[H-].[H-].[C:7]1([CH:13]2[CH2:18][CH2:17][N:16]([CH:19]3[CH2:24][CH2:23][CH:22]([C:25](OC)=[O:26])[CH2:21][CH2:20]3)[CH2:15][CH2:14]2)[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=1.C(OCC)(=O)C.O>O1CCCC1>[C:7]1([CH:13]2[CH2:14][CH2:15][N:16]([CH:19]3[CH2:24][CH2:23][CH:22]([CH2:25][OH:26])[CH2:21][CH2:20]3)[CH2:17][CH2:18]2)[CH:8]=[CH:9][CH:10]=[CH:11][CH:12]=1To a suspension of 0.36 g (9.37 mM) of lithium aluminum hydride in 50 ml of tetrahydrofuran was added a solution of 2.825 g (9.372 mM) of methyl 4-(4-phenylpiperidino)cyclohexanecarboxylate in 50 ml of tetrahydrofuran dropwise with ice-cooling and the mixture was stirred at room temperature for one hour. To this reaction mixture was added ethyl acetate with ice-cooling to decompose the excess lithium aluminum hydride. Then, water was added until a white precipitate had formed. The precipitate was filtered off with the aid of celite and washed with ethyl acetate. The filtrate and washes were pooled and the solvent was distilled off under reduced pressure. The solid residue was rinsed with diethyl ether-hexane to provide the title compound.
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