tert-butyl N-((3-(aminomethyl)phenyl)methyl)carbamate → tert-Butyl 3-((4-(4-fluorophenoxy)benzylamino)methyl)benzylcarbamate

Participants

Reaction Steps

A solution of tert-butyl 3-(aminomethyl)benzylcarbamate (0.70 g, 2.94 mmol) and 4-(4-fluorophenoxy)benzaldehyde (0.6 g, 2.78 mmol) in CH2Cl2 (15 mL) was stirred at rt under nitrogen for 40 min, and then treated with sodium triacetoxyhydroborate (1.24 g, 5.83 mmol). The resulting mixture was stirred at rt. for 3 h. The reaction mixture was concentrated and the residue was partitioned between saturated NaHCO3 solution and ethyl acetate. The organic layer (clear solution) was washed with brine, dried over MgSO4. The filtrate was concentrated and the residue was dissolved in CH2Cl2 and ethyl acetate. The solution was loaded into solid sample cartridge, vacuum dried. The sample was purified by silica gel flash chromatography. Elution with 0-30% of ethyl acetate in CH2Cl2 gave the desired product as viscous oil (0.73 g, 59%). 1H NMR (DMSO-d6): δ 7.33-7.28 (m, 2H), 7.24-7.19 (m, 5H), 7.13 (m, 1H), 7.08-7.02 (m, 2H), 6.95 (m, 2H), 4.12 (m, 2H), 3.76 (s, 4H), 1.39 (s, 9H); MS (ESI): (M+H)+=437.3.

Provenance & Evidence