Preparation of 1,2,5,6-tetra-hydro-3-carboalkoxypridines such as

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546319, C07D21174

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active

061322865

ABSTRACT:
A process is provided for the preparation of 1,2,5,6-tetrahydro-3-carboalkoxypyridines of formula (III) ##STR1## wherein R is a straight or cyclic substituted or unsubstituted alkyl chain having 1 to 6 carbon atoms, phenyl C.sub.1-6 alkyl, menthol or a derivative of menthol, or a derivative of camphor, and R' is an alkyl chain having 1 to 4 carbon atoms or phenyl C.sub.1-6 alkyl comprising reacting an alkyl pyridinium salt of formula ##STR2## wherein R and R' are as defined above and X is a suitable leaving group with sodium triacetoxyborohydride in the presence of an acid.

REFERENCES:
Dobrowsky, A., A simple synthesis of arecoline, Monaish, 1952, vol. 83, pp. 443-447, together with English abstract;.
Kozello, I.A. et al., "Improvement of the Synthesis of Arecoline From Nicotinic Acid", Khim. Farm. Zh., 1976, vol. 10, No. 11, pp. 90-91;.
Panouse, J.J., "Reduction of quaternary pyridinium salts with potassium borohydride. Application to the preparation of arecoline and determination of the structure of dihydrocodehydrases.", C.R. Acad. Sci. (Paris), 1951, v. 233, pp. 1200-1202;.
Lyle, R.E., et al., "Methyl 1-methyl-1,2,3,6-tetrahydroisonicotinate", Journal of Organic Chemistry, 1955, pp. 1761-1766;.
Gribble, G.W. et al., "Sodium Borohydride in Carboxylic Acid Media. A Review of the Synthetic Utility of Acyloxyborohydrides", Organic Preparations and Procedures Int., 17, 1985, (4-5), pp. 317-384.

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