Concise and efficient syntheses of methyl 4-(1-methylpyrrolidin-2-yl)-3-oxobutanoate and hygrine-Reference-Cited by-同舟云学术

Concise and efficient syntheses of methyl 4-(1-methylpyrrolidin-2-yl)-3-oxobutanoate and hygrine

Published:2020-04 Issue:4 Volume:98 Page:191-193
ISSN:0008-4042
Container-title:Canadian Journal of Chemistry
language:en
Short-container-title:Can. J. Chem.

Author:

Ma Xiao-Yan¹²,Huang Jian-Ping²,Yang Jing²,Liu Xingyong¹,Hu Xinjun³,Huang Sheng-Xiong¹²

Affiliation:

1. School of Chemical Engineering, and Key Laboratory of Green Chemistry of Sichuan Institutes of Higher Education, Sichuan University of Science & Engineering, Zigong 643000, P.R. China.

2. State Key Laboratory of Phytochemistry and Plant Resources in West China and CAS Center for Excellence in Molecular Plant Sciences, Kunming Institute of Botany, Chinese Academy of Sciences, Kunming 650204, P.R. China.

3. College of Mechanical Engineering, Sichuan University of Science & Engineering, Zigong 643000, P.R. China.

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.

Publisher

Canadian Science Publishing

Subject

Organic Chemistry,General Chemistry,Catalysis

Link

http://www.nrcresearchpress.com/doi/pdf/10.1139/cjc-2019-0442

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