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

Participants

Reaction Steps

A solution of cis-3-(2-pyridyl)cyclopentanol (1.86 g, 11.4 mmol) in THF (100 mL) was cooled to 0° C. and treated with phthalimide (1.85 g, 12.5 mmol), diethylazodicarboxylate (2.2 M in toluene, 5.7 mL, 11.4 mmol) and triphenylphosphine (3.29 g, 12.5 mmol). The reaction mixture was stirred at room temperature for overnight. The solvent was removed, and the crude product was purified by column chromatography (Hexane/EtOAc=3/1→2/1→1/1) to yield trans-N-[3-(2-pyridyl)cyclopentyl]phthalimide (1.52 g, 41%) as a colorless powder.

Provenance & Evidence