C(O)C.[C:4]([N:7]1[CH2:12][CH2:11][CH:10]([CH2:13][C:14](=[O:24])[C:15]2[CH:20]=[CH:19][C:18]([N:21]([CH3:23])[CH3:22])=[CH:17][CH:16]=2)[CH2:9][CH2:8]1)(=[O:6])[CH3:5].[BH4-].[Na+]>ClCCl.O>[C:4]([N:7]1[CH2:12][CH2:11][CH:10]([CH2:13][CH:14]([OH:24])[C:15]2[CH:16]=[CH:17][C:18]([N:21]([CH3:22])[CH3:23])=[CH:19][CH:20]=2)[CH2:9][CH2:8]1)(=[O:6])[CH3:5]In a solvent mixture of 60 ml of ethanol and 30 ml of water was dissolved 2.93 g of 1-acetyl-4-(4-dimethylaminobenzoylmethyl)piperidine prepared in Example 39, and at room temperature, 1 g of sodium borohydride was gradually added. The reaction mixture was diluted with dichloromethane and water for distiribution and the dichloromethane layer was dried over anhydrous magnesium sulfate. The solvent was then distilled off and the oily residue was purified by silica gel column chromatography (eluent: ethyl acetate) to give a pale yellow solid melting at 119°-120° C.
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