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Expeditious, high-yielding construction of the food aroma compounds 6-acetyl-1,2,3,4-tetrahydropyridine and 2-acetyl-1-pyrroline

TitleExpeditious, high-yielding construction of the food aroma compounds 6-acetyl-1,2,3,4-tetrahydropyridine and 2-acetyl-1-pyrroline
Publication TypeJournal Article
Year of Publication2005
AuthorsHarrison, TJ, Dake, GR
JournalJournal of Organic Chemistry
Volume70
Pagination10872-10874
Date PublishedDec
Type of ArticleArticle
ISBN Number0022-3263
KeywordsBICYCLIC ENAMINES, BREAD FLAVOR COMPONENT, COOKED RICE, HYDROLYSIS, MECHANISM, MODEL SYSTEMS, POPCORN, QUANTITATIVE-ANALYSIS, ROAST-SMELLING ODORANTS, TERTIARY ENAMINES
Abstract

The key compound responsible for the aroma of bread, 6-acetyl-1,2,3,4-tetrahydropyridine (1), has been constructed in an efficient three-step procedure from 2-piperidone in an overall yield of 56%. Compound I was liberated in the final step under basic conditions. A related synthetic route produced 2-acetyl-1-pyrroline (2), the principal component of cooked rice, in 10% overall yield.
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