Synthesis of Epibatidine

C11H13ClN2
Principal investigator | David A. Evans |
---|---|
Publication year | 2001 |
Synthesis type | Total |
Number of steps | 13 (linear) |
References |
Part 1 of 1
+
+





Sm(OTf)3
MeOH
60 °C, 12 h, 84%

Boc2O,
Et3N
CH2Cl2
RT, 3 h, 98%

n-Bu4N+ F-
THF
RT, 14 h, 81%

H2O
DMSO
130 °C, 24 h, 99%

KOTMS
PhMe
70 °C, 2 h, 72%


NaBH4
MeOH
-40 °C, 60 min, 82%
"Also isolated was the C4-epimer (7 % yield)."

MsCl,
Et3N
CH2Cl2
0 °C, 20 min, 94%


CF3CO2H
CH2Cl2
RT, 60 min, 91%

CHCl3
Reflux, 72 h, 95%
