An improved synthesis of 1-(1,2,3,6-tetrahydro-1-methyl-4-pyridinyl)ethanone, isoarecolone

✍ Scribed by J. Warren Beach

• Publisher: Journal of Heterocyclic Chemistry
• Year: 1997
• Tongue: English
• Weight: 190 KB
• Volume: 34
• Category: Article
• ISSN: 0022-152X
• DOI: 10.1002/jhet.5570340637

✦ Synopsis

Abstract

A convenient synthesis of 1‐(1,2,3,6‐tetrahydro‐1‐methyl‐4‐pyridinyl)ethanone, isoarecolone, starting with 4‐acetylpyridine is presented. 4‐Acetylpyridine was protected as the ketal followed by reaction with iodomethane to give the quaterary salt. The quaterary salt was reduced with sodium borohydride followed by deprotection to give isoarecolone in 80% overall yield.