Synthesis of Epibatidine

Structure of Epibatidine

C11H13ClN2

Principal investigator	Andrew C. Regan
Publication year	1993
Synthesis type	Total
Number of steps	7 (3 parts)
References	Tetrahedron Lett. 1993, 34, 7493.

Part 1 of 3

intermediate structure

+

intermediate structure

80-85 °C, 24 h, 36%

See the Diels-Alder Reaction

intermediate structure

H2, Pd/C

MeCN

RT, 99%

intermediate structure

Na(Hg), Na2HPO4, NaH2PO4

MeOH, THF

-78 °C to RT

"No yield given."

intermediate structure

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Part 2 of 3

intermediate structure

H2SO4, HIO4, I2

AcOH, H2O

80 °C, 53%

intermediate structure

HCl, NaNO2

H2O

0 °C to RT, 74%

See the Sandmeyer Reaction

intermediate structure

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Part 3 of 3

intermediate structure

+

intermediate structure

HCO2H, Pd(OAc)2, Ph3P, Piperidine

DMF

70 °C, 6.5 h, 35%

See the Mizoroki-Heck Reaction

intermediate structure

HBr

AcOH

RT, 22 h, 74%

intermediate structure

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