O1CCCC1.B.CO[N:9]=[C:10]([C:14]1[CH:19]=[CH:18][C:17]([Cl:20])=[CH:16][CH:15]=1)[CH:11]1[CH2:13][CH2:12]1.O.[OH-].[Na+]>C1COCC1>[Cl:20][C:17]1[CH:16]=[CH:15][C:14]([CH:10]([CH:11]2[CH2:12][CH2:13]2)[NH2:9])=[CH:19][CH:18]=1
Borane tetrahydrofuran complex (1N in THF, 65.6 mL) was added to (4-chlorophenyl)(cyclopropyl)methanone O-methyl oxime (Intermediate 2) (2.75 g) in THF (100 mL) at 25° C. under nitrogen. The resulting solution was stirred at reflux for 3 hours, then cooled to 0° C. Water was carefully added, followed by aqueous NaOH (20%, 100 mL). The resulting mixture was stirred at reflux overnight, then allowed to cool to room temperature. The product was extracted into hexane, then dried over sodium sulfate, filtered and evaporated to afford (4-chlorophenyl)(cyclopropyl)methanamine as a clear oil (2.205 g, 93%).
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