Enantiomerically pure quinuclidine derivatives and methods for t

Details Enantiomerically pure quinuclidine derivatives and methods for t Enantiomerically pure quinuclidine derivatives and methods for t

Filed on

1997-02-05

Date issued

1998-07-07

Examiner

Rotman, Alan L.

Patent Class

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

SubClass

Organic compounds

SubSubClass

Heterocyclic carbon compounds containing a hetero ring...

Other Related Categories

546 14, 546136, C07D45302, C07D45304, C07F 708

Type

Patent

Status

active

Patent number

057771227

Description

ABSTRACT:
A process for cleaving cinchona alkaloids to a quinoline derivative and an enantiomerically pure, functionalized 1-azabicyclo(2.2.2)octane, includes treating a cinchona alkaloid with a complex metal hydride while simultaneously oxidizing by exposure to air in an ether or tetrahydrofuran. Enantiomerically pure 1-azabicyclo(2.2.2)octanes of the formula ##STR1## in which R is hydrogen, a straight-chain or branched alkoxycarbonyl group with 1 to 12 carbon atoms, a straight-chain or branched alkyl group with 1 to 12 carbon atoms, alkylated silyl groups, or a substituted phenyl or benzyl substituent, are also provided.

REFERENCES:
patent: 4093619 (1978-06-01), Jarreau et al.
Hoffmann et al.,Chemical Abstracts,vol. 125(15)abst.No. 196,082v,Oct. 7, 1996.
Hoffmann et al.,Chemical Abstracts,vol. 125(5),abst.No. 50,212,Jul. 29, 1996.
Tetrahedron Letters No. 29, Oxford GB, pp. 2471-2474. G.A. Epling et al. (1977).
Chemical Abstracts, vol. 118, No. 19, May 10, 1993 pp. 923-927, A.M. Gazaliev et al.
Chemical Abstracts, vol. 108, No. 19, May 9, 1988 pp. 911-922, Y. Yanuka et al.
R.O. Hutchins, K. Learn, F. El-Telbany, Y.P. Stercho, J. Org. Chem. 1984, 49, 2438.
S. Kim, H.J. Kang, S. Yang, Tetrahedron Lett. 1984, 25, 2985.
Organic Chemistry, Third Edition, International Student Edition, 1970, pp. 425, 458 and 459.
J. Malek, M. Cherny, Syntheses 1972, 218.
H. Haubenstock, J. Org. Chem. 1973, 38, 1765.
H.C. Brown, S. Krishnamurthy, Tetrahedron 1979, 35, 567.
M. Muraki, T. Mukaiyama, Chemistry Lett. 1974, 1447.
M. Muraki, T. Mukaiyama, Chemistry Lett. 1975, 875.
R. Kanzawa, T. Tokoroyama, Syntheses 1976, 526.
J.S. Cha, J.C. Lee, H.S. Lee, S.E. Lee, J.M. Kim. O.O. Kwon, S.J. Min, Tetrahedron Lett. 1991, 32, 6903.
J.K. Ruff, M.F. Hawthorne, J. Am. Chem. Soc. 1959, 2141.
H.C. Brown and C. J. Shoaf, J. Am. Chem. Soc. 1964, 1079.
J. Koenig et al., "Nouvelle Modification de la Methode D'Oxydation Selon Oppenauer: Application a la Quinine", Tetrahedron Let., No. 31, (1978), pp. 2779-2782.
G. A. Epling et al., "Photolysis of Cinchona Alkaloids. Photochemical Degradation to 5-Vinyl-quinuclidine-2-Carboxaldehyde, A Precursor to Synthetic Antimalarials", Tetrahedron Let. No. 29, (1979), pp. 2471-2474.
K. Koch et al., "Hydroxy-Directed Hydroaluminations: A Stereoselective Approach to Cycloalkanols from .beta.-Aryl Enones", Tetrahedron Let., vol. 35, No. 8, (1994), pp. 1137-1140.
M. S. Ashwood et al., "Synthesis of the Selective Muscarinic Agonist Perkin Trans., (1985), pp. 641-644.
J. Boivin et al., "GIF Oxidation of some Alicyclic Amines", Tetrahedron Let., vol. 31, No. 16, (1990), pp. 2281-2282.

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