Acetic Anhydride → Aceclidine

Participants

Reaction Steps

A racemic mixture of (RS) 3-quinuclidinol was dissolved in acetic anhydride and refluxed for three hours to yield a racemic mixture of (RS) 3-acetoxy quinuclidine (b.p. 61°-63° C./0.26 mm Hg; 95% yield). To a boiling solution of 28.28 g of this racemic mixture was added a boiling solution of 25.1 g L-(+)-tartaric acid dissolved in 60 ml of 80% ethanol. The solution was allowed to cool to room temperature, then allowed to stand for several hours, yielding crystals of the (+) hydrogen tartrate salt of 3-acetoxy quinuclidine. This salt was recrystallized three times in 80% ethanol to give 16.77 g of colorless crystals (m.p. 93°-96° C. (froths)). In like manner, the free base obtained from the first mother liquor was then treated with R(-)-tartaric acid and recrystallized to yield 14.5 g of colorless crystals of the (-) hydrogen tartrate salt (m.p. 93°-97° C. (froths)).

Provenance & Evidence