Phthalimide → cis-N-[3-(2-pyridyl)cyclopentyl]phthalimide

Participants

Reaction Conditions

Reaction Steps

A solution of trans-3-(2-pyridyl)cyclopentanol (957 mg, 5.86 mmol) in THF (25 mL) was cooled to 0° C. and treated with phthalimide (1.29 g, 8.77 mmol), cyanomethylenetri-n-butylphosphorane (2.12 g, 8.78 mmol). The reaction mixture was stirred at 70° C. for 8 h. The solvent was removed, and the crude product was purified by column chromatography (Hexane/EtOAc=3/1→1/1) and triturated with Hexane-EtOAc to yield cis-N-[3-(2-pyridyl)cyclopentyl]phthalimide (901 mg, 53%) as a pale yellow powder.

Provenance & Evidence