[Cl:1][C:2]1[CH:9]=[CH:8][C:7]([CH2:10][CH2:11][O:12][CH3:13])=[CH:6][C:3]=1[CH:4]=O.[CH:14]1([CH2:17][NH2:18])[CH2:16][CH2:15]1.C(=O)(O)[O-].[Na+].[BH4-].[Na+]>CO>[Cl:1][C:2]1[CH:9]=[CH:8][C:7]([CH2:10][CH2:11][O:12][CH3:13])=[CH:6][C:3]=1[CH2:4][NH:18][CH2:17][CH:14]1[CH2:16][CH2:15]1To a solution of 2-chloro-5-(2-methoxyethyl)benzaldehyde from Amine 7, Step 6 (1 eq.) in methanol (0.8 M) was added 1-cyclopropylmethanamine (1.2 eq.) and sodium bicarbonate (1.5 eq). The vessel was sealed and heated at 70° C. for 2 h. The insolubles were removed via filtration and to the filtrate was then added sodium borohydride (1.5 eq.) at 0° C. The reaction mixture was allowed to warm slowly to RT overnight. The volatiles were removed in vacuo and the resulting residue was partitioned between 1 N aq. NaOH and ether. The aqueous layer was separated and back extracted with ether. The combined ethereal extracts were washed with brine, dried over Na2SO4 and filtered. Concentration of the filtrate in vacuo afforded the title compound.
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