A novel and facile route for the synthesis of medetomidine as the α2-adrenoceptor agonist

• Published in: Journal of the Iranian Chemical Society Vol. 14; no. 8; pp. 1735 - 1739
• Main Authors: Kaboudin, Babak, Haghighat, Hamideh, Aieni, Samira, Behrouzi, Leila, Kazemi, Foad, Kato, Jun-ya, Aoyama, Hiroshi, Yokomatsu, Tsutomu
• Format: Journal Article
• Language: English
• Published: Berlin/Heidelberg Springer Berlin Heidelberg 01-08-2017; Springer Nature B.V
• Subjects: Analytical Chemistry; Biochemistry; Chemical synthesis; Chemistry; Chemistry and Materials Science; Dehydration; Hydrogenation; Imidazole; Inorganic Chemistry; Methylation; Organic Chemistry; Original Paper; Physical Chemistry; Medetomidine; Wittig reaction; α; Methanone; Imidazole; adrenoceptor agonist
• ISSN: 1735-207X; 1735-2428
• DOI: 10.1007/s13738-017-1114-0

We report here a novel and facile method for the synthesis of (±)-4(5)-[1-(2,3-dimethylphenyl)ethyl]-1
H
-imidazole (medetomidine) in a good yield in five steps. The method involves Wittig olefination of the phenylimidazolylketones, followed by a hydrogenation. We demonstrate that the Wittig alkenylation reaction provides a convenient step for the synthesis of medetomidine without requiring methylation and dehydration steps, which are problematic processes in the previous methods.
Graphical Abstract
Novel route for the synthesis of medetomidine.