Organic compounds -- part of the class 532-570 series – Organic compounds – Amino nitrogen containing
Patent
1994-03-16
1995-06-20
Raymond, Richard L.
Organic compounds -- part of the class 532-570 series
Organic compounds
Amino nitrogen containing
C07C21302
Patent
active
054262275
ABSTRACT:
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. It consists of reacting 5-hydroxy-3,4-dihydro-1(2H)-naphthalenone with (R)-(-)epichlorhydrine 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.
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McClure et al. (1979) "Mode of Nucleophilic Addition to Epichlorohydrin and Related Species: Chiral Aryloxymethyloxiranes", JACS, 101:3666-3668.
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Schwender et al. (1970) "Derivatives of 3,4-Dihydro-1(2H)-naphthalenone as .beta.-Adrenergic Blocking Agents. 1 Bunolol and Related Analogs", J. Medical Chemistry, 13:684-688.
Arnalot Aguilar Carmen
Camps Garcia Pelayo
Onrubia Miguel Maria del Carmen
Stampa Diez Del Corral Alberto
Medicham, S.A.
Raymond Richard L.
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