NYCSEA

Abstract: Asymmetric organocatalysis is the use of small chiral molecules as catalysts for stereoselective reactions. Various organic molecules can be used as several unique catalysts to accelerate chemical reactions. Often, reaction intermediates are used to represent more complex chemical reactions. The intermediate used was an analogue of Chlorpheniramine. A starting material, 1-(3-methoxy-phenyl-)-pyrrolidine, was synthesized in the lab. After purifying, it was used to create (S)-3-(4-Chloro-phenyl)-3-(4-pyrolidin-1-yl-2-methoxy-phenyl)-propanol. (2S,5S)-5-bezyl-2-tert-butyl-3-methylimidazolidin-4-one (catalyst) was added to a flask along with dichloromethane and hydrochloric acid. The solution was cooled to -80 degrees Celsius using a mixture of dry ice and ethanol before adding P-chloro-cinnamaldehyde and cooling for 24 hours. TLC plating was used to determine if a new product had been formed. The solvents used in the TLC process were petroleum ether and ethanol. After the solvent had reached near the top of the chromatography paper, the solvent front was marked and the plates were stained in potassium permanganate and washed in water. Based on the results of the TLC plates, a new product was successfully created. The product contained an amine and had greater polarity than p-chloro-cinnamaldehyde and traveled less far due to the solvents being non-polar. The organocatalyst and 1-(3-methoxy-phenyl)-pyrrolidine were both visible on the plates with a dot directly below the chlorocinnamaldehyde near the starting line, meaning the reaction was successful.

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