Methyl iodide → HCID 66652988, compound

Participants

Reaction Steps

To a stirred suspension of sodium hydride (1.8 g, 0.038 mol) in dry DMF (10 mL) at 0° C., tert-butyl 3-tert-butoxy-2-[(4-cyano-2-fluorobenzyl)amino]propanoate (6.7 g, 0.019 mol) in DMF (20 mL) was added dropwise. The resulting mixture was allowed to stir for 20 min at RT. Methyl iodide (3.5 mL, 0.0057 mol) was then added dropwise at 000 and the mixture was allowed to stir for 3 hr at RT. The reaction mixture was quenched in ice water and extracted with ethyl acetate (250 mL). The organic layer was washed with water (3×100 mL), dried over sodium sulphate and concentrated under reduced pressure. The crude was purified by column chromatography using petroleum ether and ethyl acetate as eluent, affording the title compound as colorless liquid. 1H NMR (DMSO-d6, 400 MHz) δ 7.78 (d, J=9.8 Hz, 1H), 7.67 (t, J=2.5 Hz, 2H), 3.92 (d, J=15.2 Hz, 1H), 3.81-3.70 (d, J=15.0 Hz, 1H), 3.63 (m, 1H), 3.52 (m, 2H), 2.26 (s, 3H), 1.42 (s, 9H), 1.08 (s, 9H).

Provenance & Evidence