Concise and efficient syntheses of methyl 4-(1-methylpyrrolidin-2-yl)-3-oxobutanoate and hygrine
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 URL: https://www.nrcresearchpress.com/doi/abs/10.1139/cjc-2019-0442
DOI: 10.1139/cjc-2019-0442
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