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To a solution of tert-butyl (1RS,2SR)-2-hydroxy-2-[4-(pyridin-2-yloxy)phenyl]-1-[3-(1,1,2,2-tetrafluoroethoxy)benzyl]ethylcarbamate (500 mg, 0.93 mmol) was added trifluoroacetic acid (10 ml), and the mixture was stirred at 0° C. for 10 min. The reaction solution was neutralized with saturated aqueous sodium hydrogen carbonate, and extracted with ethyl acetate, (30 ml×2). The extract was washed with saturated brine, dried (anhydrous magnesium sulfate) and evaporated under reduced pressure. To a solution of the residue in acetonitrile (20 ml) were added 6,7-dihydro-5H-benzo[a]cycloheptene-1-carboxylic acid (175 mg, 0.93 mmol), 1-ethyl-3-(3-dimethylaminopropyl)carbodiimide hydrochloride (268 mg, 1.40 mmol) and 1-hydroxybenzotriazole hydrate (143 mg, 0.93 mmol), and the mixture was stirred overnight at room temperature. The reaction solution was diluted with water (150 ml), and the mixture was extracted with ethyl acetate (100 ml×2). The extract was washed successively with water and saturated brine, dried (anhydrous magnesium sulfate) and evaporated under reduced pressure. The residue was purified by silica gel column chromatography (hexane:ethyl acetate=4:1-1:1). Recrystallization from ethyl acetate-hexane gave the objective substance (181 mg, 32%).

1. extractionextracted with ethyl acetate, (30 ml×2)
2. washThe extract was washed with saturated brine
3. dry with materialdried (anhydrous magnesium sulfate)
4. customevaporated under reduced pressure
5. stirringthe mixture was stirred overnight at room temperature
6. extractionthe mixture was extracted with ethyl acetate (100 ml×2)
7. washThe extract was washed successively with water and saturated brine
8. dry with materialdried (anhydrous magnesium sulfate)
9. customevaporated under reduced pressure
10. customThe residue was purified by silica gel column chromatography (hexane:ethyl acetate=4:1-1:1)
11. customRecrystallization from ethyl acetate-hexane
12. customgave the objective substance (181 mg, 32%)