4'-Fluorobiphenyl-4-carbaldehyde → tert-Butyl 3-(((4'-fluorobiphenyl-4-yl)methylamino)methyl)benzylcarbamate

Participants

Reaction Conditions

Reaction Steps

4′-Fluorobiphenyl-4-carbaldehyde (1.0 g, 5 mmol, 1.0 eq) and tert-butyl 3-(amino methyl)benzylcarbamate (1.18 g, 5 mmol, 1 eq) were dissolved in dry methanol under nitrogen and refluxed for 4 h. The reaction mass was cooled to 0° C. and sodium borohydride (570 mg, 15 mmol, 3 eq) was added portionwise at 0° C. over 20-30 minutes. The mixture was stirred for 1 h at 0° C. and then the reaction was quenched with 10% aq. sodium bicarbonate solution. The mixture was stirred at room temperature for 1 h. The resulting solution was completely evaporated under vacuum and the aqueous layer was extracted with ethyl acetate. The organic layer was dried over anhydrous Na2SO4 and evaporated under reduced pressure. The residue was purified by silica gel (60-120) column chromatography using 5-10% methanol dichloromethane as the eluent to afford the desired compound (1.8 g, 85%) as a light yellow liquid. 1H NMR (400 MHz, DMSO-d6) δ 1.30-1.37 (d, 9H), 3.66-3.69 (d, 4H), 4.09-4.11 (d, 2H), 7.07-7.09 (d, 1H), 7.18-7.29 (m, 6H), 7.36-7.42 (m, 1H), 7.56-7.59 (m, 2H), 7.65-7.67 (d, 2H), 7.68-7.70 (m, 2H). MS (ESI): 421.0 (M+H)+.

Provenance & Evidence