Synthesis of anabaseine, salts and derivatives thereof

Details Synthesis of anabaseine, salts and derivatives thereof Synthesis of anabaseine, salts and derivatives thereof

1994-09-06

1996-06-25

Davis, Zinna Northington

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

Organic compounds

Heterocyclic carbon compounds containing a hetero ring...

546257, 546334, C07D40104, C07D21168

Patent

active

055301347

ABSTRACT:
A process for the synthesis of compounds of the formulas Ia and Ib below, wherein R.sub.1, R.sub.2, and R.sub.3, which are the same or different, are each selected from hydrogen and C.sub.1 -C.sub.4 alkyl, including the compound Anabaseine (Ia, wherein R.sub.1 =R.sub.2 R.sub.3 =H) (3,4,5,6-tetrahydro-2', 3'-bipyridine), the process comprising reacting sodium salt of .delta.-valerolactone with substituted ethyl nicotinate derivative to produce the Claisen product sodium 3-nicotinoyl-2-tetrahydropyranone enolate derivative, heating the sodium 3-nicotinoyl-2-tetrahydropyranone enolate derivative with concentrated HCl to produce 3-(5-chloro-1-pentanone-1-yl) pyridine derivative, dissolving the 3-(5-chloro-1-pentanone-1-yl) pyridine derivative in ethanol and then heating the 3-(5-chloro-1-pentanone-1-yl) pyridine derivative in ethanol with ethanolic ammonia solution in a sealed container to produce the compound Ia. Also, the process steps in the above process, and the products and intermediate products produced thereby. ##STR1##

REFERENCES:
Tetrahedron Letters, vol. 24, No. 18, pp. 1937-1940, 1983 Synthesis of Tobacco Alkaloids Via Teritiary Azides, Alberici et al.
Synthetic Communications, 2(4), 197-200 (1972), Bradford P. Mundy and Brent R. Larsen, A New Approach To Pyrrolidine and Piperidine Alkaloids.
Spath, Mamoli, 69, 1082-1085, Chemical Ber. (1936).
The Journal of Organic Chemistry, vol. 44, No. 2, Jan. 19, 1979, Aberrant Biosynthesis of 5-Fluoroanabasine from 5-Fluoro[5,6-.sup.14 C,.sup.13 C.sub.2 ]Nicotinic Acid, Established by Means of Carbon-13 Nuclear Magnetic Resonance, .sup.1, Leete, Edward.

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