Phosphorus tribromide → 1-Allyloxycarbonyl-2-methoxycarbonyl-4-trimethylsilylethynyl-3-pyrroline

Participants

Reaction Steps

To a solution of 1-allyloxycarbonyl-4-hydroxy-2-methoxycarbonyl-4-trimethylsilylethynylpyrrolidine (7.0 g) in toluene (70 ml) was slowly added phosphorus tribromide (2.25 ml) at room temperature and the mixture was stirred at room temperature for one day. The reaction mixture was then poured into iced water-ethyl acetate. The aqueous layer was then separated and extracted with ethyl acetate twice. The organic layers were combined, washed with saturated aqueous sodium hydrogen carbonate solution twice and further with water and aqueous sodium chloride solution successively, and dried over anhydrous magnesium sulfate. Finally the solvent was distilled off under reduced pressure to give 1-allyloxycarbonyl-2-methoxycarbonyl-4-trimethylsilylethynyl-3-pyrroline (3.0 g).

Provenance & Evidence