ENANTIOSELECTIVE PROCESS FOR THE PREPARATION OF LEVOBUNOLOL

ENANTIOSELECTIVE PROCESS FOR THE PREPARATION OF LEVOBUNOLOL

The invention relates to a new, industrially advantageous, process for the preparation of the known beta-adrenergic blocking agent levobunolol, not requiring resolution of racemic bunolol, based on the enantioselective synthesis of an oxiranic intermediate which is then reacted with tert-butylamine....

Ausführliche Beschreibung

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Bibliographische Detailangaben
Hauptverfasser: STAMPA DIEZ DEL CORRAL, ALBERTO, CAMPS GARCIA, PELAYO, ONRUBIA MIGUEL, MARIA DEL CARMEN, ARNALOT AGUILAR, CARMEN
Format: Patent
Sprache:eng ; fre
Schlagworte:
ACYCLIC OR CARBOCYCLIC COMPOUNDS
CHEMISTRY
METALLURGY
ORGANIC CHEMISTRY
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Beschreibung
Zusammenfassung:The invention relates to a new, industrially advantageous, process for the preparation of the known beta-adrenergic blocking agent levobunolol, not requiring resolution of racemic bunolol, based on the enantioselective synthesis of an oxiranic intermediate which is then reacted with tert-butylamine. The process of this invention consists of reacting 5-hydroxy-3,4-dihydro-1(2H)-naphthalenone with (R)-(-)epichlor-hydrine in an aprotic solvent in the presence of a strong base at a temperature of over 90.degree.C, thus obtaining the intermediate chiral oxirane (S)-5-(2,3-epoxypropoxy)-3,4-dihydro-1-(2H) --naphthalenone with more than 95% optical purity, and then, the intermediate chiral oxirane is reacted with tert-butylamine.