CordenPharma Synkem

Longvic, France

CordenPharma Synkem

Longvic, France
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Rousselin Y.,University of Burgundy | Laureano H.,CordenPharma Synkem | Clavel A.,CordenPharma Synkem
Acta Crystallographica Section E: Crystallographic Communications | Year: 2015

The title compound, C11H11FO2, 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.


Rousselin Y.,University of Burgundy | Bruel A.,CordenPharma Synkem | Clavel A.,CordenPharma Synkem
Acta Crystallographica Section E: Structure Reports Online | Year: 2012

The asymmetric unit of the title hydrated salt, C22H26F2NO4 +·Cl-·0.5H2O, consists of an (S,S,S,S)-nebivolol {nebivol = bis[2-(6-fluoro-3,4-dihydro-2H-1-benzopyran-2-yl) -2-hydroxyethyl]ammonium} cation, a chloride anion and a half-occupancy water molecule. The dihedral angle between the mean planes of the benzene rings is 50.34 (12)°. The pyran rings adopt half-chair conformations. The crystal packing features O-H⋯O hydrogen bonds and weak N-H⋯Cl, O-H⋯Cl, and O-H⋯Cl interactions, producing layers along (010).


PubMed | University of Burgundy and CordenPharma Synkem
Type: Journal Article | Journal: Acta crystallographica. Section E, Crystallographic communications | Year: 2015

The title compound, C11H11FO2, is a building block in the synthesis of the active pharmaceutical ingredient dl-nebivolol. The synthesis starting from the enanti-omerically pure (R)-6-fluoro-4-oxo-3,4-di-hydro-2H-chromene-2-carb-oxy-lic 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-di-hydro-2H-chromene-2-carb-oxy-lic 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.


Rousselin Y.,CNRS Molecular Chemistry Institute of Burgundy University | Clavel A.,CordenPharma Synkem | Bonnaventure I.,CordenPharma Synkem
Acta Crystallographica Section E: Structure Reports Online | Year: 2013

The structure of the title compound [alternatively called (R)-(-)-1-azabicyclo[2.2.2]octan-3-ol], C7H13NO, at 100 K has hexagonal (P61) symmetry. The structure shows a twist along the C - N pseudo-threefold axis. In the crystal, molecules are linked via O - H⋯N hydrogen bonds, forming infinite chains along the c-axis direction. The crystal studied was twinned by merohedry (twin law: 010, 100, 00-1; population: 0.925:0.075) © 2013.


Rousselin Y.,CNRS Molecular Chemistry Institute of Burgundy University | Laureano H.,CordenPharma Synkem | Clavel A.,CordenPharma Synkem
Acta Crystallographica Section E: Structure Reports Online | Year: 2013

The title salt, C18H21FNO2 +·Br-, determined at 115 K, crystallizes in the triclinic space group P1. The previously reported polymorph occurs in the monoclinic space group P21and has two independent molecules in the asymmetric unit [Peeters et al. (1993). Acta Cryst. C49, 2157-2160]. In the title molecule, the pyran rings adopt half-chair conformations. The absolute configuration is S for the hydroxy-bearing C atom and R for the asymmetric C atom in the dihydropyran unit. In the crystal, the components are linked by N-H⋯Br and O-H⋯Br hydrogen bonds, forming chains along the c-axis direction. The crystal studied was refined as an inversion twin.

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