Process for the preparation of isoquinoline compounds

Details Process for the preparation of isoquinoline compounds Process for the preparation of isoquinoline compounds

1997-09-05

1998-12-15

Davis, Zinna Northington

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

Organic compounds

Heterocyclic carbon compounds containing a hetero ring...

C07D21716

Patent

active

058499172

ABSTRACT:
lkanones of the formula ##STR1## wherein R is lower alkanoyl, can be produced under specific reaction conditions in a one-pot process in an advantageous manner by a Bischler-Napieralski cyclization of N-(2-cyclohex-1-enylethyl)-2-(4-methoxyphenyl)-acetamide and subsequent lower-alkanoylation of the resulting 1-(4-methoxybenzyl)-3,4,5,6,7,8-hexahydro-isoquinoline of the formula ##STR2## under an inert gas atmosphere and, if desired converted to dextomethorphan in a known manner.

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Kitamura et al., "General Asymetric Synthesis of Benzomorphans and Morphinans via Enantioselective Hydrogenation", Tetrahedron Letters, vol. 28, No. 41, pp. 4829-4832 (1987).
Kitamura et al., "General Asymetric Synthesis of Isoquinoline Alkaloids", J. Org. Chem. 59:297-310 (1994).
Schnider et al., "Synthesis of Morphinan", Helv. Chim. Acta, 33:1437-1448 (1950).
Walter et al., "Synthesis in the Class of Isoquinoline 1,2, substitute Octahydroisoquinoline", Helv. Chim. Acta, 44:1546-1554 (1961).

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