Sustainable Process for Sparteine Sulfate Preparation

Ignacio Regla, Manuel López-Ortiz, Otoniel Jiménez, Simón Hernández-Ortega, Astrid Ramírez-Betancourt, Kalina Bermúdez-Torres

Research output: Contribution to journalArticle

Abstract

(-)-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.

Original languageEnglish
JournalOrganic Process Research and Development
DOIs
StateAccepted/In press - 1 Jan 2019

Fingerprint

Sparteine
sulfates
preparation
salts
alkaloids
diamines
activity (biology)
stems
leaves
Quinolizidines
Salts
Diamines
ligands
Refrigeration
Bioactivity
Alkaloids
synthesis
Ligands

Keywords

  • (-)-sparteine sulfate
  • crystallography
  • Lupinus montanus
  • organocatalyst
  • quinolizidine alkaloids

Cite this

Regla, I., López-Ortiz, M., Jiménez, O., Hernández-Ortega, S., Ramírez-Betancourt, A., & Bermúdez-Torres, K. (Accepted/In press). Sustainable Process for Sparteine Sulfate Preparation. Organic Process Research and Development. https://doi.org/10.1021/acs.oprd.9b00379
Regla, Ignacio ; López-Ortiz, Manuel ; Jiménez, Otoniel ; Hernández-Ortega, Simón ; Ramírez-Betancourt, Astrid ; Bermúdez-Torres, Kalina. / Sustainable Process for Sparteine Sulfate Preparation. In: Organic Process Research and Development. 2019.
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Sustainable Process for Sparteine Sulfate Preparation. / Regla, Ignacio; López-Ortiz, Manuel; Jiménez, Otoniel; Hernández-Ortega, Simón; Ramírez-Betancourt, Astrid; Bermúdez-Torres, Kalina.

In: Organic Process Research and Development, 01.01.2019.

Research output: Contribution to journalArticle

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AU - Regla, Ignacio

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AU - Jiménez, Otoniel

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AU - Ramírez-Betancourt, Astrid

AU - Bermúdez-Torres, Kalina

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