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Optical Resolution of Rimantadine

1
Jiangsu Co-Innovation Center of Efficient Processing and Utilization of Forest Resources, College of Chemical Engineering, Nanjing Forestry University, Nanjing 210037, China
2
Hamari Chemicals Ltd., 1-4-29 Kunijima, Higashi-Yodogawa-ku, Osaka 533-0024, Japan
3
Department of Organic Chemistry I, Faculty of Chemistry, University of the Basque Country UPV/EHU, Paseo Manuel Lardizábal 3, 20018 San Sebastián, Spain
4
IKERBASQUE, Basque Foundation for Science, María Díaz de Haro 3, Plaza Bizkaia, 48013 Bilbao, Spain
*
Authors to whom correspondence should be addressed.
Molecules 2019, 24(9), 1828; https://doi.org/10.3390/molecules24091828
Received: 20 April 2019 / Revised: 6 May 2019 / Accepted: 11 May 2019 / Published: 12 May 2019
(This article belongs to the Section Bioorganic Chemistry)
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PDF [1740 KB, uploaded 12 May 2019]
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Abstract

This work discloses a new procedure for the resolution of commercially available racemic rimantadine hydrochloride to enantiomerically pure (S)-rimantadine using (R)-phenoxypropionic acid as a recyclable resolving reagent. Good chemical yields, operational ease, and low-cost structure underscore the preparative value of this method for the production of enantiomerically pure rimantadine for medicinal or synthetic studies. View Full-Text
Keywords: optical resolution; rimantadine; enantiomers; practicality; chiral acids and amines optical resolution; rimantadine; enantiomers; practicality; chiral acids and amines
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This is an open access article distributed under the Creative Commons Attribution License which permits unrestricted use, distribution, and reproduction in any medium, provided the original work is properly cited (CC BY 4.0).

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Han, J.; Takeda, R.; Sato, T.; Moriwaki, H.; Abe, H.; Izawa, K.; Soloshonok, V.A. Optical Resolution of Rimantadine. Molecules 2019, 24, 1828.

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