[O:1]=[C:2]1[CH2:7][CH2:6][CH:5]([C:8]2[CH:23]=[CH:22][C:11]([O:12][CH2:13][CH2:14][CH2:15][N:16]3[CH2:21][CH2:20][CH2:19][CH2:18][CH2:17]3)=[CH:10][CH:9]=2)[CH2:4][CH2:3]1.[BH4-].[Na+].C(O)(=O)C(O)=O>CO.C(O)C>[OH:1][CH:2]1[CH2:7][CH2:6][CH:5]([C:8]2[CH:23]=[CH:22][C:11]([O:12][CH2:13][CH2:14][CH2:15][N:16]3[CH2:17][CH2:18][CH2:19][CH2:20][CH2:21]3)=[CH:10][CH:9]=2)[CH2:4][CH2:3]1To a solution of 1-{3-[4-(4-oxocyclohexyl)phenoxy]propyl}piperidine (250 mg) in methanol (3 mL) is added sodium borohydride (15 mg). The mixture is stirred for two days at room temperature, then concentrated under reduced pressure and purified by column chromatography on silica gel (eluent dichloromethane/methanol/ammonia from 99.5/0.5/0.05 to 99/1/0.1) to give 179 mg of crude base which is dissolved in ethanol (2 mL). A solution of oxalic acid (50 g) in ethanol (1 mL) is added. A white precipitate appears which is filtered, rinsed with diethyl ether and dried under reduced pressure to give 127 mg of 1-{3-[4-(4-hydroxycyclohexyl)phenoxy]propyl}piperidine as a white solid
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