[F:1][C:2]([F:11])([F:10])[CH:3]1[CH2:8][CH2:7][CH2:6][CH2:5][C:4]1=O.[C:12]1([C@@H:18]([NH2:20])[CH3:19])[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1.[BH-](OC(C)=O)(OC(C)=O)OC(C)=O.[Na+].C(=O)([O-])O.[Na+]>ClCCCl>[C:12]1([C@H:18]([NH:20][C@@H:4]2[CH2:5][CH2:6][CH2:7][CH2:8][C@@H:3]2[C:2]([F:11])([F:10])[F:1])[CH3:19])[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1To a 1,2-dichloroethane solution of 2-(trifluoromethyl)cyclohexanone (10.0 g) and [(1S)-1-phenylethyl]amine (7.29 g) was added NaBH(OAc)3(25.51 g) at ambient temperature. After stirring for 2 days at ambient temperature, 150 mL of saturated aqueous sodium hydrogencarbonate was added. After extraction with EtOAc, combined organic layer was dried over MgSO4, filtered and evaporated to dryness in vacuo. The crude residue was purified by silica gel column chromatography (n-hexane:EtOAc=8:1 to 2:1) to give (1R,2S)—N-[(1R)-1-phenylethyl]-2-(trifluoromethyl)cyclohexanamine (7.83 g) as a white solid.
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