Synthesis of Epibatidine

Structure of Epibatidine

C11H13ClN2

Principal investigator	David A. Evans
Publication year	2001
Synthesis type	Total
Number of steps	13 (linear)
References	Org. Lett. 2001, 3, 3009.

Part 1 of 1

intermediate structure

+

intermediate structure

i-Pr2NEt, LiCl

MeCN

RT, 60 min, 81%

See the Horner-Wadsworth-Emmons Reaction

intermediate structure

+

intermediate structure

Me2AlCl

CH2Cl2

-78 °C, 15 min, 79%

See the Diels-Alder Reaction

intermediate structure

Sm(OTf)3

MeOH

60 °C, 12 h, 84%

intermediate structure

Boc2O, Et3N

CH2Cl2

RT, 3 h, 98%

intermediate structure

n-Bu4N+ F-

THF

RT, 14 h, 81%

intermediate structure

H2O

DMSO

130 °C, 24 h, 99%

intermediate structure

KOTMS

PhMe

70 °C, 2 h, 72%

intermediate structure

Pb(OAc)4

t-BuOH

50 °C, 3 h, 70%

See the Hofmann Rearrangement

intermediate structure

NaBH4

MeOH

-40 °C, 60 min, 82%

"Also isolated was the C4-epimer (7 % yield)."

intermediate structure

MsCl, Et3N

CH2Cl2

0 °C, 20 min, 94%

intermediate structure

LiBr

THF

Reflux, 36 h, 84%

See the Finkelstein Reaction

intermediate structure

CF3CO2H

CH2Cl2

RT, 60 min, 91%

intermediate structure

CHCl3

Reflux, 72 h, 95%

intermediate structure

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