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

Participants

Reaction Steps

Diethyl azodicarboxylate (17.4 g, 100 mmol) was added to a solution of tert-butyl 4-hydroxypiperidine-1-carboxylate (7.50 g, 37.3 mmol), 2-hydroxyisoindoline-1,3-dione (6.08 g, 37.3 mmol) and triphenylphosphine (19.6 g, 74.6 mmol) in tetrahydrofuran (100 ml) at 0° C. The reaction mixture was stirred at room temperature for 17 hours and concentrated in vacuo. The residue was purified by column chromatography (ethyl acetate/petroleum ether: 5/95 to 12.5/87.5) to give tert-butyl 4-(1,3-dioxoisoindolin-2-yloxy)piperidine-1-carboxylate (5.81 g, 45%) as a white solid: LCMS: 247 [M+1]+.

Provenance & Evidence