Process for preparing (9.alpha.,13.alpha.,14.alpha.)-1-(3-methox

Details Process for preparing (9.alpha.,13.alpha.,14.alpha.)-1-(3-methox Process for preparing (9.alpha.,13.alpha.,14.alpha.)-1-(3-methox

1997-09-03

1999-05-18

Rotman, Alan L.

Organic compounds -- part of the class 532-570 series

Organic compounds

Heterocyclic carbon compounds containing a hetero ring...

C07D221/28

Patent

active

059051531

ABSTRACT:
(9.alpha., 13.alpha.,14.alpha.)-1-(3-Methoxymorphinan-17-yl)alkanones of the formula ##STR1## wherein R signifies lower alkanoyl, are valuable intermediates for the manufacture of dextromethorphan of the formula ##STR2## They can be produced in an advantageous manner by cyclization of a (R)- or none of the formula ##STR3## with an alkylsulfonic acid or a mixture of alkylsulfonic acids at a temperature between about 5.degree. and 50.degree. C., but above the melting point of the alkylsulfonic acid used or of the alkylsulfonic acid mixture used, and can be converted into dextromethorphan in a manner known per se by cleavage or the residue R and N-methylation.

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Derwent Abstract of Japanese Patent Publication 01034964 (1997).
Kitamura et al., "General Asymetric Synthesis of Benzomorphans and Morphinans via Enantioselective Hydrogenation", Tetrahedron Letters, vol. 28, No. 41, pp. 4829-4832 (1987).
Schnider et al., "Synthesis of Morphinan", Helv. Chim Acta, 33:1437-1448 (1950).

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