Ethanol → ethyl (2R)-5-oxopyrrolidine-2-carboxylate

Participants

Reaction Conditions

Reaction Steps

To a flask containing anhydrous ethanol and D-pyroglutamic acid at ambient temperature (˜23° C.) was slowly added trimethylsilyl chloride while maintaining a reaction temperature NMT 30° C. After stirring at ambient temperature for a period of time, the reaction solution was concentrated under reduced pressure to give a yellow oil. The product was dissolved in toluene and concentrated under reduced pressure to give a yellow oil. The crude product was dissolved in dichloromethane and stirred with the slow addition of aqueous saturated sodium bicarbonate solution until a pH of 7-8 was reached. The organic layer was isolated, and the aqueous layer was extracted further with dichloromethane. The combined organic layers were dried over sodium sulfate, filtered and concentrated under reduced pressure to give product, (R)-5-oxo-pyrrolidine-2-carboxylic acid ethyl ester, as a yellow oil.

Provenance & Evidence