[H-].[Al+3].[Li+].[H-].[H-].[H-].[F:7][C:8]([F:26])([F:25])[C:9]1[CH:10]=[C:11]([C:15]2[N:16]=[C:17]([C:20](OCC)=[O:21])[S:18][CH:19]=2)[CH:12]=[CH:13][CH:14]=1.O.O.O.O.O.O.O.O.O.O.[O-]S([O-])(=O)=O.[Na+].[Na+]>O1CCCC1>[F:26][C:8]([F:7])([F:25])[C:9]1[CH:10]=[C:11]([C:15]2[N:16]=[C:17]([CH2:20][OH:21])[S:18][CH:19]=2)[CH:12]=[CH:13][CH:14]=1Under a nitrogen atmosphere at 0° C., to a solution (50 mL) of lithium aluminum hydride (710 mg, 19 mmol) in tetrahydrofuran was added dropwise a solution (40 mL) of the compound (5.6 g, 19 mmol) obtained in Example 190a in tetrahydrofuran, and the mixture was stirred at 0° C. for 3 hr. After confirmation of the termination of the reaction by TLC, sodium sulfate 10 hydrate was added to the reaction mixture, and the mixture was stirred at room temperature overnight. The resulting salt was removed and the solvent was evaporated under reduced pressure. The obtained crude product was purified by column chromatography (hexane-hexane/ethyl acetate=70/30) to give the title compound (1.2 g, 25%) as an orange oil.
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