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Concise and efficient syntheses of methyl 4-(1-methylpyrrolidin-2-yl)-3-oxobutanoate and hygrine
- Source :
- Canadian Journal of Chemistry. April, 2020, Vol. 98 Issue 4, p191, 3 p.
- Publication Year :
- 2020
-
Abstract
- Methyl 4-(1-methylpyrrolidin-2-yl)-3-oxobutanoate and hygrine are important biosynthetic intermediates for tropane alkaloids. We have developed a concise method to synthesize these two compounds from the key intermediate N-methylpyrrolinium cation. Methyl 4-(1-methylpyrrolidin-2-yl)-3-oxobutanoate and hygrine were obtained in four and six steps from commercially available 4,4-diethoxybutylamine with overall yields of 42% and 25%, respectively. Key words: methyl 4-(1-methylpyrrolidin-2-yl)-3-oxobutanoate, hygrine, biosynthetic intermediate, tropane alkaloid, N-methylpyrrolinium cation. Le 4-(1-methylpyrrolidin-2-yl)-3-oxobutanoate de methyle et l'hygrine sont des intermediaires biosynthetiques importants pour la synthese des alcaloides tropaniques. Nous avons mis au point une methode pour synthetiser ces deux composes tk;4a partir du cation N-methylpyrrolinium comme intermediaire cle. Nous avons obtenu le 4-(1-methylpyrrolidin-2-yl)-3-oxobutanoate de methyle et l'hygrine en quatre et six etapes, respectivement, a partir de la 4,4-diethoxybutylamine, qui est commercialement disponible, avec des rendements respectifs de 42 % et de 25 %. [Traduit par la Redaction] Mots-cles : 4-(1-methylpyrrolidin-2-yl)-3-oxobutanoate de methyle, hygrine, intermediaire biosynthetique, alcaloide tropanique, cation N-methylpyrrolinium.<br />Introduction Tropane alkaloids, a family of important natural products found in plants throughout the world, have attracted growing attention becauseoftheir significant biological and pharmacological activity. (1-5) These alkaloids contain complex [...]
- Subjects :
- Alkaloids
Bisphenol-A
Chemistry
Subjects
Details
- Language :
- English
- ISSN :
- 00084042
- Volume :
- 98
- Issue :
- 4
- Database :
- Gale General OneFile
- Journal :
- Canadian Journal of Chemistry
- Publication Type :
- Academic Journal
- Accession number :
- edsgcl.619740482
- Full Text :
- https://doi.org/10.1139/cjc-2019-0442