[C:1]([O:5][C:6](=[O:23])[N:7]([CH2:12][CH2:13][C:14]1[CH:19]=[CH:18][C:17]([Cl:20])=[C:16]([CH:21]=O)[CH:15]=1)[CH2:8][CH:9]([F:11])[F:10])([CH3:4])([CH3:3])[CH3:2].[CH:24]1([NH2:27])[CH2:26][CH2:25]1.[BH4-].[Na+]>CO>[C:1]([O:5][C:6](=[O:23])[N:7]([CH2:12][CH2:13][C:14]1[CH:19]=[CH:18][C:17]([Cl:20])=[C:16]([CH2:21][NH:27][CH:24]2[CH2:26][CH2:25]2)[CH:15]=1)[CH2:8][CH:9]([F:11])[F:10])([CH3:4])([CH3:3])[CH3:2]A mixture of [2-(4-chloro-3-formyl-phenyl)-ethyl]-(2,2-difluoro-ethyl)-carbamic acid tert-butyl ester (4.30 g, 12.4 mmol) and cyclopropylamine (1.77 mL, 12.4 mmol) in MeOH (125 mL) was stirred for 2 h at rt. Cyclopropylamine (0.44 mL, 6.2 mmol) was added, and the mixture was heated to reflux for 4 h. The mixture was allowed to cool to rt. NaBH4 (935 mg, 24.7 mmol) was added in portions. The mixture was stirred for 1 h. The solvents were removed under reduced pressure, and the residue was taken in EtOAc (800 mL). The resulting mixture was washed with aq. sat. NaHCO3 and brine. The org. layer was dried over MgSO4, filtered, and the solvents were removed under reduced pressure. Purification of the crude by FC (MeOH/CH2Cl2 5:95) yielded the title compound (3.53 g, 73%). LC-MS: tR=0.83 min; ES+: 389.52.
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