Water → HCID 66848216, compound

Participants

Reaction Conditions

Reaction Steps

Methytriphenylphosphonium bromide (38 g, 106 mmol) dissolved in 300 ml of toluene was cooled to 0° C., then added sodium hexamethyldisilazide (48.3 ml, 93.7 mmol) was added dropwise. After 2 hours at room temperature, The temperature was cooled to 0° C., a solution of (S)-2-(4-nitro-benzoyloxymethyl)-4-oxo-pyrrolidine-1-carboxylic acid tert-butyl ester (intermediate 56, 15.5 g, 42.6 mmol) in 300 ml of toluene was added. After 10 minutes 500 ml of water was slowly added, then reaction was allowed to reach room temperature. The organic solvent was washed with brine (500 ml), dried (Na2SO4) and evaporated to obtain crude that was purified by silica gel chromatography (petroleum ether/ethyl acetate from 15/7 to 7/1). (S)-4-Methylene-2-(4-nitro-benzoyloxymethyl)-pyrrolidine-1-carboxylic acid tert-butyl ester was obtained as yellow solid (6.82 g, yield 46%).

Provenance & Evidence