title: A Robust, Recyclable Resin for Decagram Scale Resolution of (±)-Mefloquine and Other Chiral N-Heterocycles.
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.
authors.affiliation: Laboratorium für Organische Chemie, Departement Chemie und Angewandte Biowissenschaften, ETH Zürich, Vladimir-Prelog-Weg 3, CH-8093, Zürich, Switzerland.
authors.forename: Imants
authors.initials: I
authors.lastname: Kreituss
authors.affiliation: Laboratorium für Organische Chemie, Departement Chemie und Angewandte Biowissenschaften, ETH Zürich, Vladimir-Prelog-Weg 3, CH-8093, Zürich, Switzerland.
authors.forename: Kuang-Yen
authors.initials: KY
authors.lastname: Chen
authors.affiliation: Roche Pharma Research and Early Development, preclinical CMC, Roche Innovation Center Basel, F. Hoffmann-La Roche Ltd, Grenzacherstrasse 124, CH-4070, Basel, Switzerland.
authors.forename: Simon H
authors.initials: SH
authors.lastname: Eitel
authors.affiliation: Roche Pharma Research and Early Development, preclinical CMC, Roche Innovation Center Basel, F. Hoffmann-La Roche Ltd, Grenzacherstrasse 124, CH-4070, Basel, Switzerland.
authors.forename: Jean-Michel
authors.initials: JM
authors.lastname: Adam
authors.affiliation: F. Hoffmann-La Roche Ltd, PTDCA, Process Research & Development, Bldg 65/618 A, CH-4070, Basel, Switzerland.
authors.forename: Georg
authors.initials: G
authors.lastname: Wuitschik
authors.affiliation: F. Hoffmann-La Roche Ltd, PTDCA, Process Research & Development, Bldg 65/618 A, CH-4070, Basel, Switzerland.
authors.forename: Alec
authors.initials: A
authors.lastname: Fettes
authors.affiliation: Laboratorium für Organische Chemie, Departement Chemie und Angewandte Biowissenschaften, ETH Zürich, Vladimir-Prelog-Weg 3, CH-8093, Zürich, Switzerland. bode@org.chem.ethz.ch.
authors.forename: Jeffrey W
authors.initials: JW
authors.lastname: Bode
mesh_terms: D000962:Antimalarials / Q000737:chemistry*; D006571:Heterocyclic Compounds / Q000737:chemistry*; D015767:Mefloquine / Q000737:chemistry*; D013237:Stereoisomerism
chemical_list: D000962:Antimalarials; D006571:Heterocyclic Compounds; D015767:Mefloquine
keywords: N-heterocycles; amines; enantioselective acylation; kinetic resolution; polymerization