ORGN 608 |
| Sukanta Bhattacharyya, Lanchi Vo, and Jeff W. Labadie. Department of Chemistry, Argonaut Technologies, 1101 Chess Dr, Foster City, CA 94404 |
| The selective manipulation of functional groups is central to synthetic organic chemistry. Synthesis of primary alcohols by the reduction of carboxylic acids generally requires strong reducing agents such as lithium aluminum hydride. The reaction conditions are not however compatible with other reducible functional groups such as ester, nitro, amide and epoxide. We report herein a clean reduction of polymer-supported HOBt active esters to the corresponding primary alcohols using sodium borohydride as the reducing agent. Synthesis of polymer-supported HOBt active esters was accomplished by coupling carboxylic acids with PS-HOBt (HL), a commercially available polymer-supported HOBt. Reductive cleavage of the polymer-supported active esters in the presence of sodium borohydride afforded the corresponding primary alcohols in high yields. Notable advantages of the present method include mild, chemoselective reaction conditions and simple isolation of products by a filtration. |
|
New Reactions, Methodology, Heterocycles, Aromatics
8:00 PM-10:00 PM, Wednesday, August 25, 2004 Pennsylvania Convention Center -- Hall D, Poster
Division of Organic Chemistry |