[H-].[Al+3].[Li+].[H-].[H-].[H-].[NH:7]1[C:15]2[C:10](=[CH:11][C:12]([O:16][CH:17]3[CH2:22][CH2:21][CH:20]([C:23](OCC)=[O:24])[CH2:19][CH2:18]3)=[CH:13][CH:14]=2)[CH:9]=[N:8]1.O.[OH-].[Na+]>O1CCCC1>[NH:7]1[C:15]2[C:10](=[CH:11][C:12]([O:16][CH:17]3[CH2:18][CH2:19][CH:20]([CH2:23][OH:24])[CH2:21][CH2:22]3)=[CH:13][CH:14]=2)[CH:9]=[N:8]1
Lithium aluminum hydride (52 mg, 1.39 mmol) was added to a solution of the ethyl 4-(1H-indazol-5-yloxy)cyclohexanecarboxylate (100 mg, 0.347 mmol) obtained in Example 367 in tetrahydrofuran (2 ml), and the resulting mixture was refluxed. After 2 hours, water (52 μl), a 2M-aqueous sodium hydroxide solution (0.104 ml) and then water (0.156 ml) were added to the reaction mixture, and the resulting solution was filtered by the use of Celite. The filtrate was concentrated under reduced pressure, and the resulting oil was crystallized by the addition of diisopropyl ether. The crystals were filtered under reduced pressure and then dried to obtain [4-(1H-indazol-5-yloxy)cyclohexyl]methanol (72 mg, 84%, trans/cis=4/1).
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