m-Chloroperbenzoic acid → HCID 86664649, compound

Participants

Reaction Steps

(3S)-3-Allyl-5-oxo-1-[(1R)-1-phenylethyl]pyrrolidine-3-carboxylic acid tert-butyl ester (4.9 g, 14.9 mmol) was dissolved in methylene chloride, and mCPBA (10.3 g, 59.5 mmol) was added. The mixture was stirred at room temperature for 15 hours and then heated to reflux for three hours. The solvent was evaporated under reduced pressure, and then the residue was blended with a mixture of ethyl acetate and a saturated sodium thiosulfate solution. The organic layer was washed with saturated sodium bicarbonate water, dried over magnesium sulfate, and filtered, and then the solvent was evaporated under reduced pressure. The residue was purified by silica gel chromatography (hexane/ethyl acetate=4:1→1:1) to give 4.33 g (84%) of the colorless oil title compound as a diastereomer mixture. The diastereomers were used for the next step without separation and purification.

Provenance & Evidence