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

Participants

Reaction Steps

A solution of cis-3-(3-pyridyl)cyclohexanol (5.00 g, 28.2 mmol) in THF (100 mL) was cooled to 4° C. and treated with phthalimide (4.56 g, 31.0 mmol), Diisopropylazodicarboxylate (6.10 mL, 31.0 mmol) and triphenylphosphine (8.13 g, 31.0 mmol). The reaction mixture was stirred at room temperature for 2 h. The reaction mixture was diluted with EtOAc, and washed with H2O and brine. The organic layers was dried over Na2SO4. After concentration under reduced pressure, the residue was purified by column chromatography (Hexane/EtOAc=4/1) to yield trans-N-[3-(3-pyridyl)cyclohexyl]phthalimide (5.18 g, 60%) as colorless powder.

Provenance & Evidence