N-Hydroxyphthalimide → HCID 67681828, compound

Participants

Reaction Steps

A solution of 2.94 ml (0.01755 mol) of diethyl azodicarboxylate (93%) in 10 ml of benzene is added dropwise to a mixture of 3.6 g (0.01672 mol) of cis-3-(N-BOC-amino)-cyclopentanemethanol, 2.73 g (0.01673 mol) of N-hydroxyphthalimide, 4.49 g (0.01672 mol) of triphenylphosphine and 60 ml of benzene at 20°-30° C., while stirring. After the mixture has been stirred at room temperature for 1 hour, the precipitate formed during the reaction is filtered off, the residue on the filter is suspended in benzene and the suspension is filtered again. The latter operation is repeated twice more (residue on the filter: diethyl 1,2-hydrazinedicarboxylate), and the resulting filtrates are combined and these are evaporated in vacuo. Purification of the residue is carried out by means of flash chromatography on silica gel using ethyl acetate/hexane mixtures (1:3 and 1:1). The title compound is thus obtained, m.p. 162°-163° C.

Provenance & Evidence