O.O.O.O.O.O.O.[Cl-].[Ce+3].[Cl-].[Cl-].[N+:12]([C:15]1[CH:16]=[C:17]([C:21]2[CH2:26][CH2:25][CH2:24][CH2:23][C:22]=2[CH:27]=[O:28])[CH:18]=[CH:19][CH:20]=1)([O-:14])=[O:13].[BH4-].[Na+].[Cl-].[NH4+]>CO.C1COCC1>[N+:12]([C:15]1[CH:16]=[C:17]([C:21]2[CH2:26][CH2:25][CH2:24][CH2:23][C:22]=2[CH2:27][OH:28])[CH:18]=[CH:19][CH:20]=1)([O-:14])=[O:13]Cerium chloride heptahydrate (1.22 g) was added to a mixed solution of 2-(3-nitrophenyl)cyclohex-1-enecarbaldehyde obtained in Preparation Example 4-(1) (630 mg) in methanol (60.0 mL) and THF (20.0 mL) in an ice bath. Sodium borohydride (130 mg) was added to the reaction solution at the same temperature, followed by stirring for 30 minutes. A saturated ammonium chloride solution was added to the reaction mixture, followed by extraction with ethyl acetate. The organic layer was washed with a saturated sodium chloride solution. The organic layer was dried over anhydrous magnesium sulfate. The drying agent was removed by filtration and the filtrate was concentrated under reduced pressure to obtain a crude product. The resulting crude product was purified by NH-silica gel column chromatography to obtain the title compound (610 mg).
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