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

Participants

Reaction Steps

To a solution of t-butyl 4-hydroxypiperidine-1-carboxylate (250 mg, 1.242 mmol) was added triphenylphosphine (326 mg, 1.242 mmol) and 2-hydroxyisoindoline-1,3-dione (203 mg, 1.242 mmol). After stirring at rt for 10 min, (E)-diisopropyl diazene-1,2-dicarboxylate (251 mg, 1.242 mmol) was added. After stirring at 30° C. overnight, the reaction mixture was quenched with NH4Cl (aq), extracted with EtOAc, washed with NH4Cl (aq), dried over Na2SO4, filtered and concentrated in vacuo to give a crude product, which was purified by silica gel column with gradient hexanes:EtOAc to give the title compound as a colorless oil (252 mg, 59%). LCMS (method B): [MNa]+=369, tR=2.59 min.

Provenance & Evidence