Process for the preparation of epibatidine

Details Process for the preparation of epibatidine Process for the preparation of epibatidine

1995-06-15

1996-04-23

Ivy, C. Warren

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

Organic compounds

Heterocyclic carbon compounds containing a hetero ring...

548110, 546250, 546340, 546341, 546269, C07D40100

Patent

active

055104908

ABSTRACT:
A novel 6-chloro-3-vinyl-pyridine of formula ##STR1## where X represents -H, -SO.sub.2 Ph, -CO.sub.2 Et, -COCH.sub.3 and -CHO; which is used for the synthesis of Epibatidine of formula ##STR2## by reacting said 6-chloro-3-vinyl pyridine with N-1-alkyl-2,5-di(trialkyl silyl) pyrrolidine of formula ##STR3## to obtain N-alkyl Epibatidine which is hydrogenated to obtain the Epibatidine.

REFERENCES:
Broka, C. "Total Synthesis of Epigatidine" CA 119(23) 250211c (1993).
Corey, E. G. et al. "Stereocontrolled Total", CA 120(7); 77489V (1993).
Pandey, G. et al. `Efficient Generation and 3+2! cycloaddition of cyclic azomethine glides: A general synthetic route to X-azobicyclo (m.2.1) alkane framework` Tet. Lett. 34(45) 7301-7304 (1993).
Pandey, G. et al `An expeditions synthesis of epibatidine and analogues` Tet. Lett. 35(40) 7439-7442 (1994).

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