Water → (1S,2S)-2-phenyl-cyclopropanecarboxylic acid [(S)-1-(4-bromo-phenyl)-propyl]-amide

Participants

Reaction Steps

To a solution of (1S,2S)-2-phenyl-cyclopropanecarboxylic acid (170 mg, 1.05 mmol) in dichloromethane (10 ml) was added oxallyl dichloride (145 mg, 1.2 mmol) followed by a few drops of N,N-dimethylformamide at RT. The reaction mixture was stirred at RT for 45 mins before it was concentrated down and dissolved in dichloromethane (1.5 ml). The solution was added slowly to a solution of (S)-1-(4-bromo-phenyl)-propylamine (250 mg, 1.0 mmol, HCl salt) and triethylamine (222 mg, 2.2 mmol) in dichloromethane (10 ml) at 0° C. The resulting reaction mixture was stirred at RT for 1.5 h. Water was added and the aqueous layer was extracted by dichloromethane. Organic layer was dried by magnesium sulfate and concentrated. The residue was purified via column chromatography on silica gel to afford (1S,2S)-2-phenyl-cyclopropanecarboxylic acid [(S)-1-(4-bromo-phenyl)-propyl]-amide (330 mg, 92%). 1H NMR (400 MHz, CHLOROFORM-d) δ ppm 7.37 (d, J=8.6 Hz, 2H), 7.15-7.23 (m, 2H), 7.11 (d, J=7.3 Hz, 1H), 7.08 (d, J=8.3 Hz, 2H), 6.98 (d, J=7.3 Hz, 2H), 5.75 (d, J=7.6 Hz, 1H), 4.77 (q, J=7.5 Hz, 1H), 2.31-2.41 (m, 1H), 1.65-1.81 (m, 2H), 1.48-1.59 (m, 2H), 1.12-1.23 (m, 1H), 0.82 (t, J=7.4 Hz, 3H); LRMS (ESI) (M+1)=360.04. Molecular Formula=C19H20BrNO.

Provenance & Evidence