Hydrogen Sulfide → 3-Hydroxy-3-mercaptomethylquinuclidine

Participants

Reaction Steps

U.S. Pat. No. 4,855,290 describes a process for the preparation of 2-methylspiro(1,3-oxathiolane-5,3′-quinuclidine) (1), which comprises the preparation of the epoxide of 3-methylenequinuclidine, which is subsequently reacted with hydrogen sulfide to produce 3-hydroxy-3-mercaptomethylquinuclidine and is condensed with acetaldehyde in the presence of a Lewis acid (e.g. boron trifluoride etherate) to provide 2-methylspiro(1,3-oxathiolane-5,3′-quinuclidine).

Provenance & Evidence