N-Hydroxyphthalimide → Tert-butyl 4-(1,3-dioxoisoindolin-2-yloxy)piperidine-1-carboxylate

Participants

Reaction Steps

Diethyl azodicarboxylate (40% in toluene, 2.5 ml, 5.5 mmol) was added to the mixture of N-Boc-4-hydroxypiperidine (1.0 g, 5.0 mmol), N-hydroxyphthalimide (816 mg, 5.0 mmol) and triphenylphosphine (1.3 g, 5.0 mmol) in THF (10 ml) at 0° C. and stirred at room temperature for 1.5 hours. The solvent was evaporated under reduced pressure and the residue was diluted with ethyl acetate and washed with water and brine, dried (MgSO4) and evaporated under reduced pressure. The residue was purified by column chromatography on silica (EtOAc/Hexanes 30/70-70/30) to give tert-butyl 4-(1,3-dioxoisoindolin-2-yloxy)piperidine-1-carboxylate (1.37 g, 80%).

Provenance & Evidence