Synthesis of Epibatidine

Structure of Epibatidine

C11H13ClN2

Principal investigatorAlan Armstrong
Publication year2007
Synthesis typeTotal
Number of steps 10 (linear)
References
J. Org. Chem. 2007, 72, 8019. Org. Lett. 2005, 7, 1335. Chem. Commun. 2004, 812.
Part 1 of 1
intermediate structure
NBS, TsNClNa
MeCN
RT, 60 min, 79%
intermediate structure
VinylMgBr
Et2O
-30 °C to RT, 10 min, 56%
See the Grignard Reaction
intermediate structure
SnCl4
CH2Cl2
0 °C to RT, 14.5 h, 32%
See the Prins Reaction
See the Pinacol Rearrangement
intermediate structure
H2SO4, CrO3
Acetone, H2O
0 °C to RT, 100 min, 92%
See the Jones Oxidation
intermediate structure
(COCl)2
CH2Cl2
Reflux, 20 min
intermediate structure
Special reagent
BrCCl3
hν
RT to 90 °C, 65 min, 61% (2 steps)
See the Barton Decarboxylation
intermediate structure
PhOH, HBr
H2O
Reflux, 105 min
intermediate structure
Boc2O, Na2CO3
H2O, THF
RT, 2.5 d, 67% (2 steps)
intermediate structure + intermediate structure
Special reagent
Ni(cod)2, KOt-Bu
s-BuOH
RT to 60 °C, 56%
See the Suzuki Coupling
"The yield was 66 % brsm."
intermediate structure
CF3CO2H
CH2Cl2
RT, 5 h, 89%
intermediate structure
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