Methyl iodide → HCID 69491897, compound

Participants

Reaction Steps

A mixture of 0.35 g (0.81 mmol) of (S)-[1-(4-benzyloxy-phenylcarbamoyl)-3-methylsulfanyl-propyl]-carbamic acid tert-butyl ester and 8.79 g (62.0 mmol) of methyliodide is stirred at RT for 3 d. Thereafter, the methyliodide is evaporated, the intermediate sulfonium salt dissolved in 15 ml of THF and treated with 0.79 ml (0.79 ml) of lithium bis-(trimethylsilyl)amide (1 M solution in THF) at 0° C. After stirring at 0° C. for 2 h, the reaction mixture is evaporated under reduced pressure and the solid residue is directly submitted to chromatography on silica gel using a 2:1 mixture of n-hexane and ethyl acetate as the eluent. There are obtained 0.175 mg (56% of theory) of (S)-[1-(4-benzyloxy-phenyl)-2-oxo-pyrrolidin-3-yl]-carbamic acid tert-butyl ester as a white solid. MS: m/e=383 (M+H)+.

Provenance & Evidence