Synthesis of Epibatidine
C11H13ClN2
| Principal investigator | Varinder K. Aggarwal |
|---|---|
| Publication year | 2005 |
| Synthesis type | Total |
| Number of steps | 8 (3 parts) |
| References |
Part 1 of 3
DMAP,
Boc2O
THF
Reflux, 2 h, 100%
Part 2 of 3
+
HCl,
ICl3
H2O
0 °C to RT, 100 min, 21%
+
n-BuLi
Et2O
-78 °C to RT, 5 h, 71%
""The product might still contain some LiCl.""
Part 3 of 3
+
+
DMF, Hexane(s), THF
-118 to -45 °C, 6 h, 41%
NaBH4
MeOH
-78 to -60 °C, 2.5 h, 83%
Et3N,
MsCl
CH2Cl2
RT, 4 h
CF3CO2H
CH2Cl2
RT, 15 h
CHCl3
Reflux, 48 h, 90% (3 steps)
"Two cycles were required to obtain 90 % yield."