[F:1][C:2]([F:13])([F:12])[C@H:3]1[CH2:8][CH2:7][C@H:6]([C:9](O)=[O:10])[CH2:5][CH2:4]1.[H-].[Al+3].[Li+].[H-].[H-].[H-].O.[OH-].[Na+]>O1CCCC1>[F:1][C:2]([F:12])([F:13])[C@H:3]1[CH2:4][CH2:5][C@H:6]([CH2:9][OH:10])[CH2:7][CH2:8]1trans-4-(Trifluoromethyl)cyclohexanecarboxylic acid (1.5 g, 7.65 mmol) was dissolved in tetrahydrofuran (20 mL). The reaction solution was cooled to 0° C., and lithium aluminum hydride (435 mg, 11.5 mmol) was added thereto, and then, the resulting mixture was stirred at room temperature for 3 hours. The reaction solution was cooled to 0° C., and water (0.4 mL), a 5 N aqueous solution of sodium hydroxide (0.4 mL), and water (1.2 mL) were added thereto, followed by filtration. To the filtrate, ethyl acetate was added, and the organic layer was washed with a saturated aqueous solution of sodium hydrogen carbonate and a saturated sodium chloride solution, then dried over anhydrous magnesium sulfate and filtered. Then, the solvent was distilled off under reduced pressure, whereby a crude product was obtained as a colorless oily substance (1.18 g).
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