Hydrochloric Acid → HCID 54362083, compound

Participants

Reaction Steps

A mixture of (5S,1R)-5-[(3-ethoxy-5-oxo-3-cyclohexen-1-yl)methyl]-1-(phenylmethyl)-2-pyrrolidinone and (5S,1S)-5-[(3ethoxy-5-oxo-3-cyclohexen-1-yl)methyl[-1-(phenylmethyl)-2-pyrrolidinone (150 mg, 0.46 mmol) in 10 mL of tetrahydrofuran was treated with 2 mL of 2N HCl and stirred at room temperature for 2 h, then refluxed for 1 h. The solvent was removed on a rotary evaporator and the residue was extracted with methylene chloride. The combined extracts were dried over Na2SO4 and evaporated to give 130 mg of (S)-5-[[oxo-1-(phenylmethyl)-2-pyrrolidinyl]methyl]-1,3-cyclohexanedione, mp 159°-161° C. (ethyl acetate), which was identical in all respects to that obtained in the synthesis from (E)-4-[2(S)-5-oxo-1-(phenylmethyl)-2-pyrrolidinyl]-2-butenoic acid, ethyl ester.

Provenance & Evidence