Sustainable Process for Sparteine Sulfate Preparation

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

doi:10.1021/acs.oprd.9b00379

Sustainable Process for Sparteine Sulfate Preparation

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

Centro de Desarrollo de Productos Bióticos (CEPROBI)

Research output: Contribution to journal › Article › peer-review

5 Scopus citations

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 language	English
Pages (from-to)	2567-2570
Number of pages	4
Journal	Organic Process Research and Development
Volume	23
Issue number	11
DOIs	https://doi.org/10.1021/acs.oprd.9b00379
State	Published - 15 Nov 2019

Keywords

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

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10.1021/acs.oprd.9b00379

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title = "Sustainable Process for Sparteine Sulfate Preparation",

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.",

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T1 - Sustainable Process for Sparteine Sulfate Preparation

AU - Regla, Ignacio

AU - López-Ortiz, Manuel

AU - Jiménez, Otoniel

AU - Hernández-Ortega, Simón

AU - Ramírez-Betancourt, Astrid

AU - Bermúdez-Torres, Kalina

PY - 2019/11/15

Y1 - 2019/11/15

N2 - (-)-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.

AB - (-)-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.

KW - (-)-sparteine sulfate

KW - Lupinus montanus

KW - crystallography

KW - organocatalyst

KW - quinolizidine alkaloids

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U2 - 10.1021/acs.oprd.9b00379

DO - 10.1021/acs.oprd.9b00379

M3 - Artículo

AN - SCOPUS:85074434331

SN - 1083-6160

VL - 23

SP - 2567

EP - 2570

JO - Organic Process Research and Development

JF - Organic Process Research and Development

IS - 11

ER -

Sustainable Process for Sparteine Sulfate Preparation

Abstract

Keywords

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