An efficient, enantioselective synthesis of (S)-oxybutynin using a 4-methyl-1,3-dioxane chiral auxiliary

ORGN 797

Daniel R. Clark, DANIEL.CLARK@uconn.edu and William F Bailey. Department of Chemistry, University of Connecticut, 55 N Eagleville Rd., Unit 3060, Storrs, CT 06269-3060
The synthesis of (S)-oxybutynin (1) will be discussed. The key step in the synthesis involves stereoselective addition (d.r. = 96:04) of PhMgBr to readily available, enantiopure (4R)-(+)-cis-2-cyclohexanecarbonyl-4-methyl-1,3-dioxane (2). Removal of the auxiliary by hydrolysis allows for the recovery of (R)-1,3-butanediol. Subsequent oxidation of the α-hydroxyaldehyde affords intermediate (3) with no racemization.

 

Asymmetric Reactions, Molecular Recognition, Self Assembly, Bioorganic Chemistry, Process R&D
8:00 PM-10:00 PM, Wednesday, 16 March 2005 Convention Center -- Hall D, Poster

Division of Organic Chemistry

The 229th ACS National Meeting, in San Diego, CA, March 13-17, 2005