An efficient method for the resolution of rac-VANOL by molecular complexation with (1S,2S)-(+)-diaminocyclohexane |
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| Institution: | 1. AZYP LLC, Arlington, TX, USA;2. Department of Chemistry, University of Texas at Arlington, Arlington, TX, USA;3. Department of Chemistry, Oklahoma State University, Stillwater, OK, USA;1. Department of Chemistry, Faculty of Science, Imam Khomeini International University, Qazvin, P.O. Box 288, Iran;2. Department of Chemistry, Science and Research Branch, Islamic Azad University, Tehran, Iran;1. State Key Laboratory of Drug Research, & Natural Products Chemistry Department, Shanghai Institute of Materia Medica, Chinese Academy of Sciences, Shanghai 201203, China;2. University of Chinese Academy of Sciences, Beijing 100049, China;3. School of Life Science and Technology, ShanghaiTech University, Shanghai 201203, China |
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| Abstract: | An efficient and convenient process has been developed for the resolution of VANOL using commercially available (1S,2S)-(+)-diaminocyclohexane as the resolving reagent, with (R)- and (S)-VANOL being isolated in 86% and 74% yields, respectively. The resolving reagent was recovered in 91% yield and could be reused without any decrease in its efficiency. The X-ray structural analysis of a molecular crystal consisting of (R)-VANOL and (1S,2S)-(+)-diaminocyclohexane revealed that hydrogen bonding interactions between the functional groups of the host and guest molecules dominated the stereochemistry of the guest in the molecular complex. |
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