N-Hydroxyphthalimide → HCID 178454091, compound

Participants

Reaction Steps

A solution of 6.54 ml (0.0391 mol) of diethyl azodicarboxylate (93%) in 30 ml of benzene is added dropwise to a mixture of 7.5 g (0.03726 mol) of cis-3-(N-BOC-amino)-cyclobutanemethanol, 6.08 g (0.03726 mol) of N-hydroxyphthalimide, 9.774 g (0.03726 mol) of triphenylphosphine and 120 ml of benzene at 20°-30° C., while stirring. The reaction mixture is stirred at room temperature for 2 hours and filtered, the crystalline residue (diethyl 1,2-hydrazinedicarboxylate) is washed with benzene and the filtrate is evaporated in vacuo. The residue is purified by means of flash chromatography on silica gel using ethyl acetate/hexane mixtures (1:3 and 1:2). After evaporation of the product-containing fractions and recrystallization of the residue from ethyl acetate/hexane, the title compound is obtained, m.p. 131.5°-132.5° C.

Provenance & Evidence