Synthesis of Epibatidine

Structure of Epibatidine

C11H13ClN2

Principal investigatorDavid A. Evans
Publication year2001
Synthesis typeTotal
Number of steps 13 (linear)
References
Part 1 of 1
intermediate structure + intermediate structure
i-Pr2NEt, LiCl
MeCN
RT, 60 min, 81%
intermediate structure + intermediate structure
Me2AlCl
CH2Cl2
-78 °C, 15 min, 79%
intermediate structure
Sm(OTf)3
MeOH
60 °C, 12 h, 84%
intermediate structure
Et3N, Boc2O
CH2Cl2
RT, 3 h, 98%
intermediate structure
n-Bu4N+ F-
THF
RT, 14 h, 81%
intermediate structure
H2O
DMSO
130 °C, 24 h, 99%
intermediate structure
KOTMS
PhMe
70 °C, 2 h, 72%
intermediate structure
Pb(OAc)4
t-BuOH
50 °C, 3 h, 70%
intermediate structure
NaBH4
MeOH
-40 °C, 60 min, 82%
"Also isolated was the C4-epimer (7 % yield)."
intermediate structure
Et3N, MsCl
CH2Cl2
0 °C, 20 min, 94%
intermediate structure
LiBr
THF
Reflux, 36 h, 84%
intermediate structure
CF3CO2H
CH2Cl2
RT, 60 min, 91%
intermediate structure
CHCl3
Reflux, 72 h, 95%
intermediate structure