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Optical Resolution of Rimantadine
Jianlin Han1, Ryosuke Takeda2,3, Tatsunori Sato4
1Jiangsu Co-Innovation Center of Efficient Processing and Utilization of Forest Resources, College of Chemical Engineering, Nanjing Forestry University, Nanjing 210037, China. hanjl@njfu.edu.cn.
Molecules (Basel, Switzerland)
|May 15, 2019
Summary
This study presents a new, cost-effective method for separating racemic rimantadine hydrochloride into its pure (S)-enantiomer. The process utilizes a recyclable resolving agent, making it valuable for producing pure rimantadine for medical applications.
Area of Science:
- Organic Chemistry
- Pharmaceutical Chemistry
- Chiral Separations
Background:
- Rimantadine hydrochloride is an antiviral medication typically used as a racemic mixture.
- Enantiomerically pure forms of drugs can exhibit different pharmacological profiles and reduced side effects.
- Efficient methods for chiral resolution are crucial for pharmaceutical development.
Purpose of the Study:
- To develop a novel and practical procedure for resolving racemic rimantadine hydrochloride.
- To obtain enantiomerically pure (S)-rimantadine.
- To identify a cost-effective and recyclable resolving agent.
Main Methods:
- Utilized (R)-phenoxypropionic acid as a chiral resolving reagent.
- Developed a procedure for the separation of racemic rimantadine hydrochloride.
- Investigated the recyclability of the resolving agent.
Main Results:
- Successfully resolved racemic rimantadine hydrochloride to yield enantiomerically pure (S)-rimantadine.
- Achieved good chemical yields throughout the process.
- Demonstrated the operational ease and low-cost nature of the method.
Conclusions:
- The developed procedure offers a preparatively valuable method for producing enantiomerically pure (S)-rimantadine.
- The use of (R)-phenoxypropionic acid as a recyclable reagent enhances the economic feasibility.
- This method is suitable for medicinal and synthetic studies requiring pure rimantadine.
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