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."
