A one-pot three-component reaction for the synthesis of 1-substituted-4,5-dihydro-3-alkylidenyl-pyrrolidines

ORGN 556

Wenwei Huang1, Mary-Margaret O'Donnell1, Grace Bi1, Jifeng Liu1, Libing Yu1, Carmen M. Baldino1, Andrew S. Bell2, and Toby J. Underwood2. (1) Chemistry Department, Arqule Inc, 19 presidential way, woburn, MA 01801, (2) Discovery Chemistry, Pfizer Global Research & Development, Sandwich, Kent, CT13 9NJ, United Kingdom

The Olsson three-component reaction of cyclopropylketones, aldehydes, and primary amines was investigated. Using Et2AlI at the elevated temperature, pyrrolidines, the initial products of the reaction, were completely converted to pyrrolium salts via a retro-aza-Michael reaction. The pyrrolium salts were reduced in situ giving 3-alkylidenyl-pyrrolidines. Overall, the one-pot three-component reaction provided an efficient way for the synthesis of 3-alkylidenylpyrrolidines.

Combinatorial, parallel, and solid-phase chemistry 1:00 PM-5:00 PM, Wednesday, March 31, 2004 Anaheim Convention Center -- 303A, Oral Division of Organic Chemistry The 227th ACS National Meeting, Anaheim, CA, March 28-April 1, 2004