Synthesis of Epibatidine

Structure of Epibatidine

C11H13ClN2

Principal investigatorAlan Armstrong
Publication year2007
Synthesis typeTotal
Number of steps 10 (linear)
References
Part 1 of 1
intermediate structure
NBS, TsNClNa
MeCN
RT, 60 min, 79%
intermediate structure
VinylMgBr
Et2O
-30 °C to RT, 10 min, 56%
intermediate structure
SnCl4
CH2Cl2
0 °C to RT, 14.5 h, 32%
See the Prins Reaction
intermediate structure
CrO3, H2SO4
Acetone, H2O
0 °C to RT, 100 min, 92%
See the Jones Oxidation
intermediate structure
(COCl)2
CH2Cl2
Reflux, 20 min
intermediate structure
BrCCl3
RT to 90 °C, 65 min, 61% (2 steps)
intermediate structure
HBr, PhOH
H2O
Reflux, 105 min
intermediate structure
Na2CO3, Boc2O
H2O, THF
RT, 2.5 d, 67% (2 steps)
intermediate structure + intermediate structure
KOt-Bu, Ni(cod)2
s-BuOH
RT to 60 °C, , 56%
See the Suzuki Coupling
"The yield was 66 % brsm."
intermediate structure
CF3CO2H
CH2Cl2
RT, 5 h, 89%
intermediate structure