p-Toluenesulfonic acid → (5S)-5-(Hydroxymethyl)-3,3-dimethylpyrrolidin-2-one

Participants

Reaction Steps

A mixture of 27.15 g I.46 (3,3,6,6-tetramethyl-tetrahydro-pyrrolo[1,2-c]oxazol-5-one) and 0.282 g p-toluenesulfonic acid in 500 ml methanol was stirred at reflux overnight. The mixture was concentrated. Additional 500 ml methanol and 2.8 g p-toluenesulfonic acid were added and the mixture was stirred 4 h at reflux. The mixture was diluted with water and treated with sodium carbonate to obtain a basic pH. The organic layer was separated, dried with magnesium sulfate and concentrated to give 1 g (60% content; 3% of theory)

Provenance & Evidence