Process for the preparation of azanoradamantane benzamides

Details Process for the preparation of azanoradamantane benzamides Process for the preparation of azanoradamantane benzamides

1995-05-19

1997-07-22

Trinh, Ba K.

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

Organic compounds

Carboxylic acid esters

C07C 6974

Patent

active

056505353

ABSTRACT:
A process for the preparation of a .gamma.-lactone of the formula ##STR1## which can be used to produce a single enantiomer of aminoazanoradamantane which is coupled to aromatic acid moieties to produce compounds useful as 5-HT agonists or antagonists.

REFERENCES:
patent: 5140023 (1992-08-01), Becker et al.
patent: 5223613 (1993-06-01), Becker et al.
Daniel L. Flynn, et al. "New AZA(NOR) Adamantanes are Agonists at the Newly Identified Serotonin 5-HT4 Receptor and Antagonists at the 5-HT3 Receptor" Bioorganic & Medicinal Chemistry Letters, vol. 2, No. 12, pp. 1613-1618, 1992.
Gunter Helmchen, et al. "Building Blocks for the Synthesis of Enantiomerically Pure Jasmonoids: Synthesis of (+)-Methyl Epijasmonate**" Angew. Chem. Int. Ed. Engl. 29, (1990) No. 9, pp. 1024-1025.
Horst Hartmann, et al. "High Stereoselectivity in Lewis-Acid-Catalyzed and Uncatalyzed Diels-Alder Reactions of the Fumarate of (S) Ethyl Lactate**" Angew. Chem. Int. Ed. Engl. 26, (1987), No. 11, pp. 1143-1145.
Gunter Helmchen, et al "Asymmetric Diels-Alder Reactions with Chiral Enoates as Dienophiles", Modern Synthctic Methods 1986, vol. 4, pp. 263-306.
D. L. Flynn et al. Use of Atom-Transfer Radical Cyclizations as an Efficient Entry into a New "Serotonergic" Azanoradamantane, Tetrahedron Letters, vol. 33, No. 48, 1992, Oxford GB, pp. 7283-7286.
J. Neumeister et al. Ozone Cleavage of Olefins with Formation of Ester Fragments, Angewandte Chemie International Edition,, vol. 17, No. 12, 1978 Weinheim De, pp. 939-940.
Abstract--Database WPI, Derwent Publications Ltd., London, GB; AN 92-069451 and JP, A, 04 013 663 (Sumitomo Seiyaku KK), Jan. 17, 1992.

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