705291-21-0Relevant academic research and scientific papers
Chiral Vicinal Diamines Derived from Mefloquine
Boratyński, Przemys?aw J.,Kowalczyk, Rafa?,Kucharski, Dawid J.
, p. 10654 - 10664 (2021)
Novel 1,2-diamines based on the mefloquine scaffold prepared in enantiomerically pure forms resemble 9-amino-Cinchona alkaloids. Most effectively, 11-aminomefloquine with an erythro configuration was obtained by conversion of 11-alcohol into azide and hydrogenation. Alkylation of a secondary amine unit was needed to arrive at diastereomeric threo-11-aminomefloquine and to introduce diversity. Most of the substitution reactions of the hydroxyl group to azido group proceeded with net retention of the configuration and involved actual aziridine or plausible aziridinium ion intermediates. Enantiomerically pure products were obtained by the resolution of either the initial mefloquine or one of the final products. The evaluation of the efficacy of the obtained vicinal diamines in enantioselective transformations proved that erythro-11-aminomefloquine is an effective catalyst in the asymmetric Michael addition of nitromethane to cyclohexanone (up to 96.5:3.5 er) surpassing epi-aminoquinine in terms of selectivity.
RESOLUTION OF MEFLOQUINE WITH O,O-DI-P-AROYLTARTARIC ACID
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Page 4, (2008/06/13)
A process for increasing the optical purity of a mixture of enantiomers of mefloquine, used a substantially single enantiomer of a O, O-di-p-aroyltartaric acid as a resolving agent.
