N-Hydroxyphthalimide → (S)-3-(1,3-Dioxo-1,3-dihydro-isoindol-2-yloxy)-pyrrolidine-1-carboxylic acid tert-butyl ester

Participants

Reaction Steps

Diethyl azodicarboxylate (17.4 g, 100 mmol) was added to a solution of (R)-tert-butyl 3-hydroxypyrrolidin-1-carboxylate (9.40 g, 50.0 mmol), 2-hydroxyisoindoline-1,3-dione (8.16 g, 50.0 mmol) and triphenylphosphine (26.2 g, 100 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 (S)-tert-butyl 3-(1,3-dioxoisoindoline-2-yloxy)pyrrolidin-1-carboxylate (6.74 g, 41%) as a white solid: LCMS: 277 [M−55]+.

Provenance & Evidence