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A Robust,Recyclable Resin for Decagram Scale Resolution of (±)‐Mefloquine and Other Chiral N‐Heterocycles |
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| Authors: | Imants Kreituss Dr Kuang‐Yen Chen Dr Simon H Eitel Dr Jean‐Michel Adam Dr Georg Wuitschik Dr Alec Fettes Prof?Dr Jeffrey W Bode |
| Institution: | 1. Laboratorium für Organische Chemie, Departement Chemie und Angewandte Biowissenschaften, ETH Zürich, Zürich, Switzerland;2. Roche Pharma Research and Early Development, preclinical CMC, Roche Innovation Center Basel, F. Hoffmann-La Roche Ltd, Basel, Switzerland;3. F. Hoffmann-La Roche Ltd, PTDCA, Process Research & Development, Basel, Switzerland;4. http://www.bode.ethz.ch/ |
| Abstract: | Decagram quantities of enantiopure (+)‐mefloquine have been produced via kinetic resolution of racemic mefloquine using a ROMP‐gel supported chiral acyl hydroxamic acid resolving agent. The requisite monomer was prepared in a few synthetic steps without chromatography and polymerization was safely performed on a >30 gram scale under ambient conditions. The reagent was readily regenerated and reused multiple times for the resolution of 150 grams of (±)‐mefloquine and other chiral N‐heterocylces. |
| Keywords: | amines enantioselective acylation kinetic resolution N-heterocycles polymerization |