Hydrochloric Acid → benzyl (2R, 4R)-2-(4,5-diphenyloxazol-2-yl)-4-methoxypyrrolidine-1-carboxylate

Participants

Reaction Steps

To a solution of benzyl (2R, 4R)-2-(4,5-diphenyloxazol-2-yl)-4-hydroxypyrrolidine-1-carboxylate (400 mg) and CH3I (0.57 mL) in DMF (5 mL) was added NaH (60% oil suspension, 48 mg) at 5° C. The mixture was stirred at the same temperature for 10 minutes, then stirred at room temperature for 30 minutes. The reaction mixture was poured into diluted HCl, and extracted with EtOAc. The organic layer was washed with water, saturated sodium hydrogen carbonate, water and brine, dried (MgSO4), and evaporated in vacuo. The residue was purified by silica gal column chromatography (hexane-EtOAc, 1:1 elution) to give benzyl (2R, 4R)-2-(4,5-diphenyloxazol-2-yl)-4-methoxypyrrolidine-1-carboxylate (402.9 mg).

Provenance & Evidence