Synthesis of 1-(p-carbomethoxyphenyl)-3-pyrrolidinone by a Diels-Alder route

EC Taylor, K McDaniel, JS Skotnicki

Index: Taylor, Edward C.; McDaniel, Keith; Skotnicki, Jerauld S. Journal of Organic Chemistry, 1984 , vol. 49, # 13 p. 2500 - 2501

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Citation Number: 10

Abstract

Treatment of methyl p-aminobenzoate with dimethyl sulfide, followed immediately by the addition of N-chlorosuccinimide in CH2C12 at-25" C, gave a white slurry, which, upon extraction with 5% sodium hydroxide, gave a solution of the sulfilimine 2 (Scheme I). Oxidation of 2 in situ at 0" C to methyl p-nitrosobenzoate (3) was accomplished by addition of 1.2 equiv of m-chloroperbenzoic acid. Diels-Alder reaction of 3 with 2-methoxy-1, 3- ...