[F:1][C:2]([F:28])([F:27])[C:3]1[CH:22]=[C:21]([C:23]([F:26])([F:25])[F:24])[CH:20]=[CH:19][C:4]=1[CH2:5][N:6]1[C:12](=[O:13])[CH2:11][CH2:10][CH:9]([C:14](OCC)=[O:15])[CH2:8][CH2:7]1.[BH4-].[Li+].O>C1COCC1>[F:28][C:2]([F:1])([F:27])[C:3]1[CH:22]=[C:21]([C:23]([F:26])([F:25])[F:24])[CH:20]=[CH:19][C:4]=1[CH2:5][N:6]1[CH2:7][CH2:8][CH:9]([CH2:14][OH:15])[CH2:10][CH2:11][C:12]1=[O:13]To a solution of ethyl 1-[2,4-bis(trifluoromethyl)benzyl]-7-oxoazepane-4-carboxylate (14.8 g) in THF (400 mL) was added lithium borohydride (4.5 g). The reaction mixture was stirred at 50° C. for 1 hr, water was added, and the mixture was extracted with ethyl acetate. The extract was dried over anhydrous sodium sulfate, and the solvent was evaporated under reduced pressure to give the title compound (12.0 g).
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