Sodium Carbonate → (2R, 4R)-(+)-2-(ethoxycarbonyl)-4-hydroxy-1-(4-methoxy phenethyl) pyrrolidine

Participants

Reaction Conditions

Reaction Steps

To a suspension of 6.60 g (33.7 mmol) of (2R,4R)-(+)-2-(ethoxycarbonyl)-4-hydroxypyrrolidine hydrochloride in acetonitrile (60 ml) were added 8.22 g (77.6 mmol) of sodium carbonate, 4-methoxyphenethyl bromide (8.71 g, 40.5 mmol), and sodium iodide (150 mg, 1.0 mmol) and the mixture was stirred at 40-45° C. for 65 h. The mixture was concentrated in vacuo and water was added to the residue, and the products were extracted with ethyl acetate. The extract was washed with saturated aqueous sodium chloride and the products were extracted with 10% aqueous hydrochloride. The extract was washed with ethyl acetate, basified with potassium carbonate and extracted with ethyl acetate. The organic layer was washed with saturated aqueous sodium chloride, dried over anhydrous sodium sulfate, and concentrated in vacuo to obtain oily (2R, 4R)-(+)-2-(ethoxycarbonyl)-4-hydroxy-1-(4-methoxy phenethyl)pyrrolidine (5.85 g, 59.1%).

Provenance & Evidence