Originally posted by Sauron
Here are the reaction schemes. The first is the Edgewood patentfor 3-quinuclinol from 4-vinylpyridine. Conversion to the glycol by aq KMnO4 or an
improvement as suggested by Ritter, peracetic acid; conversion to HCl salt (not shown) and catalytic hydrogenation, then cyclodehydration over basic
alumina in vapor phase.
My modification is to chlorinate the glycol alpha-hydroxyl selectively via Org.Syn., then proceed as above to obtain the unscheduled compound
3-chloroquinuclidine.
Ritter says he prefer hypochlorite addition to the vunylic pi bond but that leaves the Cl in the beta position always. Thus far he has not elaborated
how he would cyclize that compound (not shown) to the 3-hydroxyquinuclidine. |