Reduction of ethyl benzoylacetate and selective protection of 2-(3-hydroxy-1-phenylpropyl)-4-methylphenol: A new and facile synthesis of tolterodine

KA De Castro, J Ko, D Park, S Park…

Index: De Castro, Kathlia A.; Jungnam, Ko; Daejong, Park; Sungdae, Park; Hakjune, Rhee Organic Process Research and Development, 2007 , vol. 11, # 5 p. 918 - 921

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Citation Number: 18

Abstract

A new and facile synthesis of tolterodine using ethyl benzoylacetate as the starting material was developed. Reduction using sodium borohydride in methanol followed by Friedel– Crafts alkylation utilizing FeCl3· 6H2O as catalyst lead to the known 2-(3-hydroxy-1- phenylpropyl)-4-methylphenol intermediate. Consecutive protection of phenolic OH with p- toluenesulfonyl chloride via two-phase reaction and conversion of aliphatic OH using p- ...