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Abstract

Chiral synthesis of centrally acting muscle relaxant (S)-mephenesin was achieved using L-proline catalyzed a-aminoxylation of 3-(2-methyl-phenxoy)propanal as chirality induction step. The chiral synthesis started with commercially available 2-cresol and was accomplished in four steps with overall yield 56%. The enantiomeric excess of final product (S)-mephenesin is >98%. The chiral purity was determined by chiral-HPLC using Chiralcel-OD column. The synthesis involves oxidation of primary alcohol to aldehyde with iodoxybenzoic acid (IBX) as one of the steps.

Keywords

Mephenesin Organocatalysis L-Proline a-Aminoxylation Aldehyde Iodoxybenzoic acid.

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P. Panchgalle, S., S. More, V., S. Bondge, A., & I. Momin, K. (2022). Organocatalytic Chiral Synthesis of Centrally Acting Muscle Relaxant (S)-Mephenesin. Asian Journal of Organic & Medicinal Chemistry, 7(2), 231–234. https://doi.org/10.14233/ajomc.2022.AJOMC-P394
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