Methyl iodide → HCID 59400094, compound

Participants

Reaction Steps

Sodium hydride (0.1 g, 4.16 mmol) was added to a 0° C. solution of tert-butyl 1-(3,4-dichlorobenzyl)-1,2,3,4-tetrahydroquinolin-3-ylcarbamate (0.85 g, 2.09 mmol) and iodomethane (95%, 2.97, 10 eq) in anhydrous tetrahydrofuran (10 mL). The mixture was stirred at room temperature for 1 hour. The mixture was quenched by slowly adding few drops of water. The resulting mixture was dried over anhydrous sodium sulfate and the solvent evaporated. The residue was purified by flash chromatography (eluted with 5% EtOAc in hexane) to give tert-butyl 1-(3,4-dichlorobenzyl)-1,2,3,4-tetrahydroquinolin-3-yl(methyl)carbamate as white solid (789 mg). 1H NMR (DMSO) 400 MHz δ 7.57 (d, J=4 Hz, 1H), 7.61 (brd, J=6.4 Hz, 1H), 7.47 (d, J=1.6, 1H), 7.23 (dd, J=2.0 Hz and 8.4 Hz, 1H), 6.95 (d, J=7.6 Hz, 1H), 6.91 (m, 1H), 6.53 (m, 1H), 6.45 (d, 8.4 Hz, 1H), 4.45 (brd, J=10.4 Hz, 1H), 4.29 (br, 1H), 3.40 (t, 10.4 Hz, 1H), 3.21 (m, 1H), 3.02 (m, 1H), 2.74 (m, 1H), 2.72 (s, 3H), 1.36 (m, 9H). LCMS m/e 422 (M+H).

Provenance & Evidence