Hydrochloric Acid → 2-chloro-4-phenyl-6,7-dihydro-5H-cyclopenta[b]pyridine-3-carbonitrile

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Reaction Steps

Under argon, 500 mg (2.12 mmol) of the compound from Example 16A, 0.57 ml (4.25 mmol) of isopentyl nitrite and 571 mg (4.25 mmol) of copper(II) chloride in 21 ml of tetrahydrofuran were heated under reflux for 6 h. After cooling, 1 N hydrochloric acid was added and the reaction mixture was extracted with ethyl acetate. The organic phase was washed with water and a saturated aqueous sodium chloride solution, dried over magnesium sulfate and freed from the solvent on a rotary evaporator. The residue was purified by preparative HPLC (column: YMC GEL ODS-AQ S-5, 15 μm; mobile phase gradient: acetonitrile/water 10:90→95:5).

Provenance & Evidence