1-Azabicyclo[2.2.2]oct-2-ene-3-carboxylic acid methyl ester hydrochloride synthesis

Yield:-

Reaction Conditions:

with thionyl chloride

Steps:

14.c (c)

(c) Preparation of 3-Methoxycarbonyl-1-azabicyclo[2.2.2]oct-2-ene hydrochloride Powdered 3-hydroxy-3-methoxycarbonyl-1-azabicyclo[2.2.2]octane (16.0 g, 0.086 mol) was added protionwise to thionyl chloride (100 ml) at 0°. Following the addition, the reaction mixture was stirred and heated under reflux for 48 h. The thionyl chloride was then removed under reduced pressure to afford a solid, which was recrystallized from acetone, giving 3-methoxycarbonyl-1-azabicyclo[2.2.2]oct-2-ene hydrochloride, m.p. 178°-179°.

References:

US4328234,1982,A