atropine

Place synthetic routes below This is another Charles Igwe's contribution on Atroprin



The route of synthesis shown here is gulded by the FGA analysis. The FGA result predicted the atropine is formed by reaction of j-trpinol and tropic acid.[ Fischer-Speier Estertification] j-trpinol is FGA model shows it can be made form j-tripone which is prodyuced for the reaction predictied by Schὄpf by reaction of 1,4 butanone +metyl amine and Penta-3-one-1,5, dicaroxylic acid in controlled pH condensation reaction [ buffer is used for the pH control] The yield of trewcation is pretty high 90% producing tripone. The tripone is then reduced by Zn/HI in the stereo selective reduction route to gibe j- tripnol Tropic acid is prepared by the Blicket.al route using Phenyl acetic acid as the starting material Which is then subsequently treated with Grignard reagent and followed by addition of HCHO producing Tropic acid. The steroseclectivity and lower no of intermediate steps of reaction involved gives the better yield of synthesis system **Ref= A guide book for Organic Synthesis - Ian Fleming**





By Ashleybeth Martinez, Charles Igwe, and Lanny Lantigua Dr. B We did the following changes as you advised. Ashleybeth and Lanny Work cited: Wade "Claisen condensation" page 1068-1070



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MaximizeSettingsLoading... Ashleybeth, Charles, and Lanny: The first PDF that you show is the classic way it was done before Robinson. I remember when I first saw the synthesis presented I was surprised that they got any product at all after all of the steps. It is really amazing that all of this is reduced into one or two steps in the Robinson method. The third PDF wories me a little. I don't think that you can get away with using a grignard reagent in the presence of a carboxylic acid. You should consider a claisen type condensation instead. That alpha proton should be even more acidic with aromatic next to it. You would have to use an ethyl ester and sodium ethoxide to get it to work. Of course formaldehyde doesn't have any alpha protons, so that sould not be a problem. Bruce Bondurant The acid synthesis looks better. I still a carbon appear out of nowhere when you convert the cyanohydrin to a chloride.