Synthesis of Epibatidine

Structure of Epibatidine

C11H13ClN2

Principal investigatorAndrew C. Regan
Publication year1993
Synthesis typeTotal
Number of steps 7 (3 parts)
References
Part 1 of 3
intermediate structure + intermediate structure
80-85 °C, 24 h, 36%
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
Part 2 of 3
intermediate structure
H2SO4, HIO4, I2
AcOH, H2O
80 °C, , 53%
intermediate structure
HCl, NaNO2
H2O
0 °C to RT, , 74%
intermediate structure
Part 3 of 3
intermediate structure + intermediate structure
HCO2H, Pd(OAc)2, Ph3P, Piperidine
DMF
70 °C, 6.5 h, 35%
See the Heck Coupling
intermediate structure
HBr
AcOH
RT, 22 h, 74%
intermediate structure