Triethylamine → HCID 10446037, compound

Participants

Reaction Steps

A solution of 0.8 g (3.0 mmol) of methyl 7-hydroxy-5-[2-(3-pyridyl)ethyl]-heptanoate in 3 ml methylene chloride is cooled to 0° and 0.52 mL (3.7 mmol) triethylamine is added followed by 0.26 mL (3.3 mL) methanesulfonyl chloride. The reaction mixture is stirred at 0° for 30 minutes and then 1.65 g (25 mmol) finely powdered potassium cyanide is added followed by 15 mL dimethyl sulfoxide. After stirring for 30 minutes the cold bath is removed and the mixture is stirred at room temperature for 18 hours. The reaction mixture is poured on to saturated aqueous ammonium chloride solution and then extracted with ethyl acetate (3×70 mL). Combined organic phase is washed with water (4×60 mL), brine (60 mL) and dried (MgSO4), filtered and evaporated to give an oil which is purified by flash chromatography to give both the desired methyl 7-cyano-5-[2-(3 -pyridyl)ethyl]-heptanoate and the mesylate of the starting alcohol. The mesylate is subjected to the cyanide displacement conditions described above to yield additional methyl 7-cyano-5-[2-(3-pyridyl)-ethyl]-heptanoate.

Provenance & Evidence