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A Stepwise Approach to 1,4,10,13-Tetraaza-18-Crown-6 Ether
Pieter Troosters1,2, Lara Bruneel1,2, Wim Dehaen2
1Nuclear Energy Technology, Belgian Nuclear Research Centre (SCK CEN), Mol, Belgium.
None:
A two-step approach to the synthesis of tetraaza-18-crown-6 ether was evaluated to address the limitations of the currently used one-step macrocyclization, such as low yield due to substantial side product formation. In this route, the reaction conditions were optimized, reducing cyclization to the undesired nine-membered ring by a factor of eight. This resulted in a 50% yield for the two-step macrocyclization, or 28% when column chromatography was avoided, both significantly higher than the 16% yield obtained when reproducing the one-step method.
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The acid-catalyzed addition of alcohol to an alkene involves treating the alkene with an excess of alcohol in the presence of an acid catalyst to form an ether under suitable conditions. The hydrogen will add to the less substituted carbon so that the nucleophile can attack the more...
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