Potassium Carbonate → HCID 69630562, compound

Participants

Reaction Conditions

Reaction Steps

A mixture of α-bromo-α-(4-chlorophenyl)acetic acid methyl ester (2.63 g, 10 mmol), (R)-1-(4-chlorophenyl)ethylamine (1.55 g, 10 mmol), potassium carbonate (2.76 g, 20 mmol), and tetrabutylammonium iodide (500 mg, 1.35 mmol) in dry acetonitrile (10 mL) was heated at 45° C. for 12 h. After the mixture was cooled at room temperature, the solvent was evaporated in vacuo. Then, the residue was partitioned between ice-cold water (50 mL) and ethyl acetate (70 mL). The aqueous layer was extracted twice with additional ethyl acetate (2×50 mL) and dried (Na2SO4). After evaporation of the solvent, the residue was chromatographed on silica (EtOAc/hexanes, 5:95 to 15:85), then converted to the HCl salt to give the title compound as a colorless powder (2.5 g, 74%, mixture of two diastereomers): 1H NMR (400 MHz, CD3OD) δ 1.74 (t, J=6.8 Hz, 3H, CH3), 3.69 (s, 1.5 H, 0.5 CH3), 3.82 (s, 1.5 H, 0.5 CH3), 4.41 (q, J=6.8 Hz, 0.5 H, 0.5 CH), 4.49 (q, J=6.8 Hz, 0.5 H, 0.5 CH), 4.99 (s, 0.5 H, 0.5 CH), 5.12 (s, 0.5 H, 0.5 CH), 7.42–7.56 (m, 8H, ArH). Mass spectrum (LCMS, ESI pos.): Calcd for C17H17Cl2NO2: 337.0; found: 338.0 (M+H)+.

Provenance & Evidence