Sustainable Process for Sparteine Sulfate Preparation,Organic Process Research & Development

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Sustainable Process for Sparteine Sulfate Preparation
Organic Process Research & Development ( IF 3.1 ) Pub Date : 2019-10-22 , DOI: 10.1021/acs.oprd.9b00379
Ignacio Regla ₁ , Manuel López-Ortiz ₁ , Otoniel Jiménez ₁ , Simón Hernández-Ortega ₂ , Astrid Ramírez-Betancourt ₃ , Kalina Bermúdez-Torres ₃

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(−)-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.

中文翻译：

可持续制备硫酸parteine的方法

（-）-斯巴特丁硫酸盐是喹is嗪手性二胺生物碱（-）-斯巴丁碱的稳定盐。该化合物除了具有各种生物活性外，还已成功地用于不对称合成中的对映选择性锂化反应中的配体和有机催化剂。即使在冷藏中，（-）-天冬氨酸的游离碱也会逐渐变质，但是其稳定的盐（-）-天冬氨酸硫酸盐在处理和储存方面具有优势。据我们所知，文献中没有从羽扇豆属的物种中获得（-）-硫酸parteine的方法。在这项工作中，我们提出了一个有效且可持续的过程，以从羽扇豆羽扇豆的叶片和茎中获得（-）-硫酸天冬氨酸和游离碱（-）-天冬氨酸。

更新日期：2019-10-23

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