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Named reactions

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Epibatidine

Chemical structure of Epibatidine
C11H13ClN2
Author Varinder K. Aggarwal
Publication year 2005
Synthesis type Total synthesis
Number of steps 8 (3 parts)
Reference

Browse hundreds of other total syntheses.

Part 1 of 3
Chemical structure
Boc2O, DMAP
THF
Reflux, 2 h, 100%
Chemical structure

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Part 2 of 3
Chemical structure
ICl3, HCl
H2O
0 °C to RT, 100 min, 21%
Chemical structure + Chemical structure
n-BuLi
Et2O
-78 °C to RT, 5 h, 71%

"The product might still contain some LiCl."
Chemical structure

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Part 3 of 3
Chemical structure
+
Chemical structure
Reagent structure
THF, DMF, Hexane(s)
-118 to -45 °C, 6 h, 41%

Selectivity : >95:05 dr, 97:03 er
Chemical structure
NaBH4
MeOH
-78 to -60 °C, 2.5 h, 83%
Chemical structure
MsCl, Et3N
CH2Cl2
RT, 4 h
Chemical structure
CF3CO2H
CH2Cl2
RT, 15 h
Chemical structure
CHCl3
Reflux, 48 h, 90% (3 steps)

Two cycles were required to obtain 90 % yield.
Chemical structure

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