Ethyl bromoacetate → HCID 69891019, compound

Participants

Reaction Steps

To a 0° C. solution of (S)-(−)-1-(4-methoxyphenyl)ethylamine (25 g, 165 mmol) and Et3N (46 mL, 330 mmol) in THF (350 mL) was added a solution of ethyl bromoacetate (27.5 mL, 248 mmol) in THF (50 mL) dropwise over 30 min. The reaction mixture was allowed to warm to room temperature, stirred overnight, then diluted with EtOAc and washed with water and a saturated NaCl solution. The organic layer was dried (Na2SO4) and concentrated under reduced pressure to give ethyl 2-{[(1S)-1-(4-methoxyphenyl)ethyl]amino}acetate (40 g, 100%) as a colorless oil: TLC (40% EtOAc/hex) Rf 0.4; 1H NMR (CDCl3) δ 1.25 (t, J=7.2 Hz, 3H), 1.37 (d, J=6.6 Hz, 3H), 2.03 (br s, 1H), 3.21 (d, J=17.6 Hz, 1H), 3.29 (d, J=17.6 Hz, 1H),), 3.76 (q, J=6.6 Hz, 1H), 3.81 (s, 3H), 4.16 (q, J=7.2 Hz, 2H), 6.87 (d, J=8.7 Hz, 2H), 7.23 (d, J=8.7 Hz, 2H); 13C NMR (CDCl3) δ 14.1, 24.2, 48.8, 55.2, 57.0, 60.6, 113.8, 127.8, 136.6, 158.7, 172.6; HPLC ES-MS m/z (rel abundance) 238 (MH+, 100%).

Provenance & Evidence