Methyl iodide → HCID 15884726, compound

Participants

Reaction Steps

To a solution of 2-hydroxymethyl-5-(2-methoxyphenyl)-N-(carbobenzyloxy)-tetrahydropyrrole (2.49 g, 7.30 mmol) in DMF (20 mL) at 0-40° C. was added methyl iodide (4.55 mL, 73 mmol) and NaH (60% oil dispersion, 1.75 g, 43.8 mmol) and the resulting suspension was stirred at room temperature for 1 hour. The reaction mixture was quenched with H2O at 0° C., ether was added, and the aqueous layer was extracted with ether (×4), and the combined organic layers were washed with brine, dried over anhydrous Na2SO4, and concentrated in vacuo. The crude product was purified by silica gel flash chromatography (5% EtOAc-95% hexanes) to provide the title compound as a colorless oil. 1H NMR (CDCl3, 400 MHz) δ: 3.77 (3H, s, OMe), 3.38 (3H, s, OMe).

Provenance & Evidence