A new approach towards 1-phenyl and 1-benzyl substituted 2-(aminomethyl)cyclopropanecarboxamides as novel derivatives of the antidepressant Milnacipran
2-(2-Cyano-2-phenylethyl)aziridines were converted into novel trans-2-aminomethyl-1-phenylcyclopropanecarboxamides via regiospecific ring opening and 3-exo-tet cyclisation, thus providing the first convenient entry into the trans-isomer of Milnacipran as a useful template for further derivatisation. Furthermore, unprecedented 2-aminomethyl-1- benzylcyclopropanecarboxamides have been synthesized using two different routes starting from 2-(2-cyanoethyl)aziridines, both involving α-benzylation with respect to the nitrile group and aziridine to cyclopropane ring transformation. The Royal Society of Chemistry 2009.
Vervisch, Karel,D'Hooghe, Matthias,Toernroos, Karl W.,De Kimpe, Norbert
experimental part
p. 3271 - 3279
(2009/10/24)
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