Sustainable Process for Sparteine Sulfate Preparation

(−)-Sparteine sulfate is a stable salt of the quinolizidine chiral diamine alkaloid (−)-sparteine. This compound, in addition to presenting various biological activities, has successfully been used as a ligand and organocatalyst in enantioselective lithiation reactions in asymmetric synthesis. (−)-S...

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Bibliographic Details
Published in:Organic process research & development 2019-11, Vol.23 (11), p.2567-2570
Main Authors: Regla, Ignacio, López-Ortiz, Manuel, Jiménez, Otoniel, Hernández-Ortega, Simón, Ramírez-Betancourt, Astrid, Bermúdez-Torres, Kalina
Format: Article
Language:English
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Summary:(−)-Sparteine sulfate is a stable salt of the quinolizidine chiral diamine alkaloid (−)-sparteine. This compound, in addition to presenting various biological activities, has successfully been used as a ligand and organocatalyst in enantioselective lithiation reactions in asymmetric synthesis. (−)-Sparteine free base deteriorates gradually, even in refrigeration, but its stable salt, (−)-sparteine sulfate, offers advantages in handling and storage. To the best of our knowledge, no process exists in the literature for obtaining (−)-sparteine sulfate from the species of the plant genus Lupinus. In this work, we present an efficient and sustainable process to obtain (−)-sparteine sulfate and free base (−)-sparteine from leaves and stems of Lupinus montanus.
ISSN:1083-6160
1520-586X
DOI:10.1021/acs.oprd.9b00379