[CH:1]1([NH2:4])[CH2:3][CH2:2]1.[Cl:5][C:6]1[CH:18]=[CH:17][C:9]([CH2:10][NH:11][C:12]([CH:14]2[CH2:16][CH2:15]2)=[O:13])=[CH:8][C:7]=1[CH:19]=O.[BH4-].[Na+].[OH-].[Na+]>CO>[Cl:5][C:6]1[CH:18]=[CH:17][C:9]([CH2:10][NH:11][C:12]([CH:14]2[CH2:16][CH2:15]2)=[O:13])=[CH:8][C:7]=1[CH2:19][NH:4][CH:1]1[CH2:3][CH2:2]1Cyclopropylamine (1.39 mL, 19.8 mmol) was added to a sol. of cyclopropanecarboxylic acid 4-chloro-3-formyl-benzylamide (3.13 g, 13.2 mmol) in MeOH (28 mL). The mixture was stirred overnight, and NaBH4 (996 mg, 26.0 mmol) was added in portions. The mixture was stirred for 3 h, and aq. 1M NaOH (70 mL) was added. The solvents were partially removed under reduced pressure, and the aq. residue was extracted with EtOAc (2×). The combined org. extracts were washed with brine, dried over MgSO4, filtered, and the solvents were removed under reduced pressure. Purification of the crude by FC (CH2Cl2→MeOH/CH2Cl2 1:9) yielded the title compound (3.37 g, 92%). LC-MS: tR=0.62 min; ES+: 279.35.
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