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Named reactions

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Search synthesis

Epibatidine

Chemical structure of Epibatidine
C11H13ClN2
Author David A. Evans
Publication year 2001
Synthesis type Total synthesis
Number of steps 13 (linear)
Reference

Browse hundreds of other total syntheses.

Part 1 of 1
Chemical structure
+
Chemical structure
i-Pr2NEt, LiCl
MeCN
RT, 60 min, 81%

See the Horner-Wadsworth-Emmons Reaction
Chemical structure + Chemical structure
Me2AlCl
CH2Cl2
-78 °C, 15 min, 79%

Selectivity : 95:05 dr
See the Diels-Alder Reaction
Chemical structure
Sm(OTf)3
MeOH
60 °C, 12 h, 84%
Chemical structure
Boc2O, Et3N
CH2Cl2
RT, 3 h, 98%
Chemical structure
n-Bu4N+ F-
THF
RT, 14 h, 81%
Chemical structure
H2O
DMSO
130 °C, 24 h, 99%
Chemical structure
KOTMS
PhMe
70 °C, 2 h, 72%
Chemical structure
Pb(OAc)4
t-BuOH
50 °C, 3 h, 70%

See the Hofmann Rearrangement
Chemical structure
NaBH4
MeOH
-40 °C, 60 min, 82%

Also isolated was the C4-epimer (7 % yield).
Chemical structure
MsCl, Et3N
CH2Cl2
0 °C, 20 min, 94%
Chemical structure
LiBr
THF
Reflux, 36 h, 84%

See the Finkelstein Reaction
Chemical structure
CF3CO2H
CH2Cl2
RT, 60 min, 91%
Chemical structure
CHCl3
Reflux, 72 h, 95%
Chemical structure

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