Pyridine → tert-Butyl 3-(hydroxyimino)pyrrolidine-1-carboxylate

Participants

Reaction Steps

1.87 g of hydroxylamine hydrochloride and 3.3 ml of pyridine were added to a solution of 2.0 g of 1-(t-butoxycarbonyl)-3-pyrrolidone in 9 ml of ethanol, and the mixture was refluxed for 2 hours. The solvent was then distilled off from the reaction mixture, saturated aqueous sodium bicarbonate solution was added to the residue, and it was extracted with chloroform. The chloroform extract was dried over anhydrous magnesium sulfate and the solvent was distilled off. The residue was chromatographed on a silica gel column, using a 2/1 mixture of benzene and ethyl acetate as eluent, giving 1.482 g of 1-(t-butoxycarbonyl)-3-hydroxyiminopyrrolidine as a mixture of syn- and anti-isomers.

Provenance & Evidence