An Improved and Simple Route for the Synthesis of 3-Quinuclidinone Hydrochloride

Title:An Improved and Simple Route for the Synthesis of 3-Quinuclidinone Hydrochloride

Volume: 12 Issue: 4

Author(s): Jigar Y. Soni, V. Premasagar and Sonal Thakore

Affiliation:

Keywords: 3-quinuclidinone hydrochloride, Dieckmann reaction, isonepecotic acid, Gram scale synthesis.

Abstract: An improved method for the synthesis of 3-quinuclidinone hydrochloride 4 from piperidine-4-carboxylic acid 1 has been described. Reaction of piperidine-4-carboxylic acid 1 with thionyl chloride and ethanol gave ethyl piperidine 4-carboxylate 2. It was further condensed with methyl chloroacetate in presence of sodium carbonate to give ethyl 1-(2-methoxy-2- oxoethyl)piperidine-4-carboxylate 3. One pot Dieckmann reaction of 3 in presence of potassium tertbutoxide followed by hydrolysis and decarboxylation gave title compound azabicyclo[2.2.2]oct-3-one hydrochloride 4.

Cite this article as:

Soni Y. Jigar, Premasagar V. and Thakore Sonal, An Improved and Simple Route for the Synthesis of 3-Quinuclidinone Hydrochloride, Letters in Organic Chemistry 2015; 12 (4) . https://dx.doi.org/10.2174/1570178612666150113231048