4-Fluorobenzaldehyde → HCID 58531569, compound

Participants

Reaction Steps

To a solution of tert-butyl 3-(aminomethyl)-5-(4-fluorophenoxy)benzylcarbamate (1.37 g, 3.96 mmol) in CH2Cl2 (15 mL) and 2-propanol (15 mL) was added 4-fluorobenzaldehyde (0.42 mL, 3.96 mmol). The reaction mixture was stirred at rt. under nitrogen for 40 min, and then treated with sodium triacetoxyhydroborate (1.76 g, 8.31 mmol). The resulting mixture was stirred at rt for 2 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 and dried over MgSO4. The filtrate was concentrated. The sample was purified by flash chromatography. Elution with 0-35% of ethyl acetate in CH2Cl2 gave the product as viscous oil (1.2 g, 67%). 1H NMR (CD3OD): δ 7.35-7.32 (m, 2H), 7.13-6.99 (m, 7H), 6.87 (s, 1H), 6.80 (s, 1H), 4.20 (s, 2H), 3.70 (s, 2H), 1.44 (s, 9H); MS (ESI): (M−H)−=513.1.

Provenance & Evidence