[NH:1]1[CH:5]=[CH:4][N:3]=[N:2]1.[H-].[Na+].[F:8][C:9]1[CH:14]=[CH:13][C:12]([C@@:15]2([CH2:19][N:20]3[CH:24]=[N:23][CH:22]=[N:21]3)[C@H:17]([CH3:18])[O:16]2)=[CH:11][CH:10]=1>CN(C)C=O>[F:8][C:9]1[CH:14]=[CH:13][C:12]([C@:15]([OH:16])([C@H:17]([N:2]2[N:3]=[CH:4][CH:5]=[N:1]2)[CH3:18])[CH2:19][N:20]2[CH:24]=[N:23][CH:22]=[N:21]2)=[CH:11][CH:10]=1To a stirred solution of 1H-1,2,3-triazole (1.49 g) in dimethylformamide (35 ml) was added portionwise 60% sodium hydride in oil (0.63 g) under ice-cooling. Ten minutes later, to the mixture was added (2R,3S)-2-(4-fluorophenyl)-3-methyl-2-[(1H-1,2, 4-triazol-1-yl)methyl]oxirane (3.34 g), followed by stirring for 4 hours at 80° C. After cooling, the mixture was concentrated. The residue was partitioned with ethyl acetate (300 ml) and saturated saline. The organic layer was washed with saturated saline, dried and distilled under reduced pressure. The residue was purified by silica gel column chromatography (silica gel 150 g, eluent: dichloro methane/acetone=3:2>1:1). The first eluate gave Compound 36 (1.02 g), followed by recrystallization from dichloromethane-diisopropyl ether to afford colorless prisms. Then a second eluate gave Compound 37 (1.05 g), followed by recrystallization from dichloromethane-diisopropyl ether to afford a colorless crystalline powder.
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