Synthesis of Epibatidine

Structure of Epibatidine

C11H13ClN2

Principal investigatorVarinder K. Aggarwal
Publication year2005
Synthesis typeTotal
Number of steps 8 (3 parts)
References
Part 1 of 3
intermediate structure
DMAP, Boc2O
THF
Reflux, 2 h, 100%
intermediate structure
Part 2 of 3
intermediate structure
HCl, ICl3
H2O
0 °C to RT, 100 min, 21%
intermediate structure + intermediate structure
n-BuLi
Et2O
-78 °C to RT, 5 h, 71%
""The product might still contain some LiCl.""
intermediate structure
Part 3 of 3
intermediate structure + intermediate structure
DMF, Hexane(s), THF
-118 to -45 °C, 6 h, 41%
intermediate structure
NaBH4
MeOH
-78 to -60 °C, 2.5 h, 83%
intermediate structure
Et3N, MsCl
CH2Cl2
RT, 4 h
intermediate structure
CF3CO2H
CH2Cl2
RT, 15 h
intermediate structure
CHCl3
Reflux, 48 h, 90% (3 steps)
"Two cycles were required to obtain 90 % yield."
intermediate structure