909396-90-3Relevant academic research and scientific papers
Stereocontrolled synthesis of trisubstituted cyclopropanes: Expedient, atom-economical, asymmetric syntheses of (+)-bicifadine and DOV21947
Xu, Feng,Murry, Jerry A.,Simmons, Bryon,Corley, Edward,Fitch, Kenneth,Karady, Sandor,Tschaen, David
, p. 3885 - 3888 (2007/10/03)
An expedient, atom-economical, asymmetric synthesis of 1-aryl-3- azabicyclo[3.1.0]hexanes, including (+)-Bicifadine and DOV21947, in a single-stage through process without isolation of any intermediates has been developed. The key of this synthesis is the in-depth mechanistic understanding of the complicated epoxy nitrile coupling at each reaction stage. Therefore, the desired trisubstituted cyclopropane can be prepared in high ee and yield by controlling the reaction pathway through manipulating the nitrile anion aggregation state.
METHODS AND COMPOSITIONS FOR PRODUCTION, FORMULATION AND USE OF 1-ARYL-3-AZABICYCLO[3.1.0] HEXANES
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Page/Page column 57-58, (2010/11/23)
The invention provides novel l-aryl-3-azabicyclo[3.1.0] hexanes that are active for modulating biogenic amine transport, along with compositions and methods for using these compounds to treat central nervous system disorders. Certain l-aryl-3-azabicyclo[3.1.0] hexanes are provided that have at least one substituent on the aryl ring. In other embodiments l-aryl-3-azabicyclo[3.1.0] hexanes are provided that have a substitution on the nitrogen at the '3' position. In additional embodiments l-aryl-3-azabicyclo[3.1.0] hexanes are provided which have one substitution on the aryl ring, as well as a substitution on the nitrogen at the '3' position. The invention also provides novel methods of making aryl- and aza-substituted l-aryl-3-azabicyclo[3.1.0] hexanes, including synthetic methods that form novel intermediate compounds of the invention for producing aryl- and aza-substituted l-aryl-3-azabicyclo[3.1.0] hexanes.
