Cargando…

Crystal structure of (R)-6-fluoro-2-[(S)-oxiran-2-yl]chroman

The title compound, C(11)H(11)FO(2), is a building block in the synthesis of the active pharmaceutical ingredient dl-nebivolol. The synthesis starting from the enanti­omerically pure (R)-6-fluoro-4-oxo-3,4-di­hydro-2H-chromene-2-carb­oxy­lic acid resulted in a mixture of two stereoisomers, namely (R...

Descripción completa

Detalles Bibliográficos
Autores principales: Rousselin, Yoann, Laureano, Hugo, Clavel, Alexandre
Formato: Online Artículo Texto
Lenguaje:English
Publicado: International Union of Crystallography 2015
Materias:
Acceso en línea:https://www.ncbi.nlm.nih.gov/pmc/articles/PMC4571392/
https://www.ncbi.nlm.nih.gov/pubmed/26396792
http://dx.doi.org/10.1107/S205698901501261X
Descripción
Sumario:The title compound, C(11)H(11)FO(2), is a building block in the synthesis of the active pharmaceutical ingredient dl-nebivolol. The synthesis starting from the enanti­omerically pure (R)-6-fluoro-4-oxo-3,4-di­hydro-2H-chromene-2-carb­oxy­lic acid resulted in a mixture of two stereoisomers, namely (R)-6-fluoro-2-[(S)-oxiran-2-yl]chroman and (R)-6-fluoro-2-[(R)-oxiran-2-yl]chroman. The mixture was separated by column chromatography but only one stereoisomer crystallized. The X-ray structure analysis revealed that the solid consisted of the R,S isomer. A similar procedure was repeated for (S)-6-fluoro-4-oxo-3,4-di­hydro-2H-chromene-2-carb­oxy­lic acid and, in this case, the S,R isomer was produced as a crystalline solid. Thus, all four stereoisomers of the title epoxide were obtained and their absolute configuration was assigned. The crystal studied was refined as an inversion twin.