title: Synthesis of desfluorinated nebivolol isomers.
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.
authors.affiliation: §MOLISA GmbH, Universitätsplatz 2, 39106 Magdeburg, Germany.|∥Salutas Pharma GmbH, Otto-von-Guericke Allee 1, 39179 Barleben, Germany.
authors.forename: Purushothama Chary
authors.initials: PC
authors.lastname: Khandavalli
authors.affiliation: †Chemisches Institut, Otto-von-Guericke-Universität, Universitätsplatz 2, 39106 Magdeburg, Germany.|§MOLISA GmbH, Universitätsplatz 2, 39106 Magdeburg, Germany.
authors.forename: Oliver
authors.initials: O
authors.lastname: Spiess
authors.affiliation: §MOLISA GmbH, Universitätsplatz 2, 39106 Magdeburg, Germany.
authors.forename: Oliver M
authors.initials: OM
authors.lastname: Böhm
authors.affiliation: ‡Corden Pharma International GmbH, Otto-Hahn-Strasse, 68723 Plankstadt, Germany.
authors.forename: Ilia
authors.initials: I
authors.lastname: Freifeld
authors.affiliation: ‡Corden Pharma International GmbH, Otto-Hahn-Strasse, 68723 Plankstadt, Germany.
authors.forename: Kurt
authors.initials: K
authors.lastname: Kesseler
authors.affiliation: ‡Corden Pharma International GmbH, Otto-Hahn-Strasse, 68723 Plankstadt, Germany.
authors.forename: Gerhard
authors.initials: G
authors.lastname: Jas
authors.affiliation: †Chemisches Institut, Otto-von-Guericke-Universität, Universitätsplatz 2, 39106 Magdeburg, Germany.|§MOLISA GmbH, Universitätsplatz 2, 39106 Magdeburg, Germany.
authors.forename: Dieter
authors.initials: D
authors.lastname: Schinzer
mesh_terms: D000959:Antihypertensive Agents / Q000138:chemical synthesis* / Q000737:chemistry; D007536:Isomerism; D000068577:Nebivolol / Q000138:chemical synthesis* / Q000737:chemistry; D013237:Stereoisomerism
chemical_list: D000959:Antihypertensive Agents; D000068577:Nebivolol