2. Academic Validation
  3. Synthesis of desfluorinated nebivolol isomers

Synthesis of desfluorinated nebivolol isomers

  • J Org Chem. 2015 Apr 17;80(8):3965-73. doi: 10.1021/acs.joc.5b00263.
Purushothama Chary Khandavalli 1 2,  Oliver Spiess 3 1,  Oliver M Böhm 1,  Ilia Freifeld 4,  Kurt Kesseler 4,  Gerhard Jas 4,  Dieter Schinzer 3 1
Affiliations

Affiliations

  • 1 §MOLISA GmbH, Universitätsplatz 2, 39106 Magdeburg, Germany.
  • 2 ∥Salutas Pharma GmbH, Otto-von-Guericke Allee 1, 39179 Barleben, Germany.
  • 3 †Chemisches Institut, Otto-von-Guericke-Universität, Universitätsplatz 2, 39106 Magdeburg, Germany.
  • 4 ‡Corden Pharma International GmbH, Otto-Hahn-Strasse, 68723 Plankstadt, Germany.
PMID: 25826147 DOI: 10.1021/acs.joc.5b00263
Abstract

The syntheses of all possible stereoisomers of desfluorinated side products of the potent antihypertensive β-blocker nebivolol are reported. A straightforward approach using a common racemic precursor was employed to obtain the desired optically active building blocks. For one series of compounds, a Sharpless asymmetric epoxidation (SAE) route yielded in a direct fashion the required compounds whereas a Mitsunobu reaction was selected to obtain the Other series of compounds. This offers a flexible approach to all desfluoronebivolol side-products in order to fully characterize them.

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