tert-Butanol → 1-Benzyl-3-(tert-butoxycarbonylamino)pyrrolidine

Participants

Reaction Steps

1-benzylpyrrolidin-3-ylamine (10 g, 57 mmol) was dissolved in 3M aqueous sodium hydroxide solution (21 ml) and t-butanol (114 ml) in a 500 ml vessel, and t-butyl-dicarbonate ((t-Boc)2O; 13.07 g, 59.9 mmol) was added thereto while stirring. The resulting mixture was reacted for 12 hrs. After the completion of the reaction, the reaction product was extracted with ethyl acetate twice. The organic layer was separated, washed with 0.1N hydrochloric acid solution and brine in order, dried over anhydrous sodium sulfate, filtered and concentrated under reduced pressure. The residue thus obtained was subjected to a silica gel column chromatography to obtain 15.25 g of the title compound as a white solid (yield 97%).

Provenance & Evidence