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

doi:10.1107/S205698901501261X

Paper

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

Published Jul 8, 2015 · Yoann Rousselin, Hugo Lauréano, Alexandre Clavel

Acta Crystallographica Section E: Crystallographic Communications

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Abstract

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.

Study Snapshot

The crystal structure of (R)-6-fluoro-2-[(S)-oxiran-2-yl]chroman reveals all four stereoisomers and their absolute configuration, aiding in the synthesis of dl-nebivolol.

PopulationOlder adults (50-71 years)

Sample size24

MethodsObservational

OutcomesBody Mass Index projections

ResultsSocial networks mitigate obesity in older groups.

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Paper

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

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References

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OLEX2 is a portable, workflow-oriented software for determining, viewing, and analyzing molecular crystal structures, benefiting both chemists and crystallographers.

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Chemoenzymatic synthesis of four diastereomers of (6-fluoro-2-chromanyl) oxirane: An intermediate of a potent β-blocker

The study successfully synthesized optically active 5-acetoxy-3-(p-fluorophenoxy)-1-pentanol 4 and its diastereomers, which are important intermediates for the synthesis of potent -blocker R-67555.

A short history of SHELX.

SHELX has evolved from SHELX-76 to the present day, incorporating useful innovations and enduring popularity in various molecular applications.

Citations

Investigations of 6-Fluoro-4-Oxo-3,4-Dihydro-2H-Chromene-2-Carboxylic Acid by Quantum Computational, Spectroscopic, TD-DFT with Various Solvents and Molecular Docking Studies

This study reveals the molecular structure and properties of 6-Fluoro-4-Oxo-3,4-dihydro-2H-chromene-2-carboxylic acid (FODHCC), a key molecule in biological studies like molecular docking and drug similarity.