[C:1]1([N:7]2[C:11]([NH:12][S:13]([C:16]3[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=3)(=[O:15])=[O:14])=[CH:10][C:9]([C:22](OCC)=[O:23])=[N:8]2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[H-].C([Al+]CC(C)C)C(C)C.Cl>O1CCCC1.C1(C)C=CC=CC=1>[OH:23][CH2:22][C:9]1[CH:10]=[C:11]([NH:12][S:13]([C:16]2[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=2)(=[O:15])=[O:14])[N:7]([C:1]2[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=2)[N:8]=1A solution of ethyl 1-phenyl-5-[(phenylsulfonyl)amino]-1H-pyrazole-3-carboxylate (445 mg) in tetrahydrofuran (10 mL) was cooled to −78° C., and a 1.5 mol/L solution (4 mL) of diisobutylaluminum hydride in toluene was added dropwise. After stirring at 0° C. for 1 hr, the mixture was treated with 1 mol/L hydrochloric acid, and extracted with ethyl acetate. The aqueous layer was extracted with ethyl acetate again, and the combined extracts were washed with 1.0 mol/L hydrochloric acid, water and saturated brine, dried over anhydrous sodium sulfate, and concentrated under reduced pressure. The residue was purified by silica gel column chromatography (eluent:hexane-ethyl acetate=1:1→1:3) to give the title compound as a pale-yellow oil (yield 379 mg, yield 96%).
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