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

Participants

Reaction Steps

1-benzylpyrrolidin-4-ylamine (10 g, 57 mmol) was dissolved in 3M sodium hydroxide aqueous 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) wad added thereto while stirring. The resulting mixture was reacted at room temperature for 12 hrs, extracted with ethyl acetate twice. The organic layer was separated, washed with 0.1N hydrochloric acid solution and brine, 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