Citric Acid → HCID 57758716, compound

Participants

Reaction Conditions

Reaction Steps

Sodium hydride (60% in oil, 76.1 mg, 1.74 mmol) and a solution of tert-butyl (3S)-3-methyl-4-methylene-5-oxo-1-[(1R)-1-phenylethyl]pyrrolidine-3-carboxylate (500 mg, 1.59 mmol) in dimethylsulfoxide (24 mL) were added sequentially to a solution of trimethylsulfonium iodide (401 mg, 1.82 mmol) in dimethylsulfoxide (8 mL), and the mixture was stirred at 90° C. for 30 minutes. 10% Aqueous citric acid (32 mL) and water (96 mL) were added to the reaction mixture at room temperature, followed by extraction with ethyl acetate (200 mL×2). The obtained organic layer was washed sequentially with water (100 mL) and saturated brine (100 mL). The organic layer was dried over sodium sulfate anhydrate. After filtration, the filtrate was evaporated to dryness under reduced pressure. The residue was purified through silica gel column chromatography (eluent; hexane:ethyl acetate 3:1 to 2:1), to thereby yield the title compound as colorless crystals (315 mg, 60.3%). 1H-NMR and IR spectral data of this product were found to coincide with those obtained in Example 5.

Provenance & Evidence