Phthalimide → Triphenylphosphine Oxide

Participants

Reaction Steps

A solution of biphenyl-2-yl((2S,4R)-4-hydroxy-2-(hydroxymethyl)pyrrolidin-1-yl)methanone (1.67 g, 5.6 mmol), phthalimide (1.24 g, 8.4 mmol) and triphenylphosphine (2.20 g, 8.4 mmol) in THF (56 mL) was cooled to 0° C. and added with diisopropyl azodicarboxylate (DIAD; 1.63 mL, 8.4 mmol) dropwise. The resulting suspension was allowed to warm to rt gradually and stirred overnight, concentrated in vacuo to a brown oil which was eluted on silica gel column (70% EtOAc in Hexanes) to provide 2-(((2S,4R)-1-(biphenylcarbonyl)-4-hydroxypyrrolidin-2-yl)methyl)isoindoline-1,3-dione as a white solid contaminated with triphenylphosphine oxide and used as-is.

Provenance & Evidence