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Paper | Regular issue | Vol 43, No. 6, 1996, pp.1189-1199
Published online, 1st January, 1970
DOI: 10.3987/COM-96-7395
Synthesis of a Carbon-14 Ring-labeled Benzthiophene via Degradation and Recyclization of an Unlabeled Benzthiophene

Scott W. Landvatter

*SmithKline Beecham, Synthetic Chemistry Department, Radiochemistry Section, P.O.Box 1539, UW 2830, King of Prussia, PA 19406, U.S.A.

Abstract

Synthesis of 7-chloro-2-ethyl-3,4,5,6-tetrahydro-4-methyl-[2-14C]thieno[4,3,2-ef][3]benzazepine (1) has been accomplished via degradation,alkylation and recyclization of an unlabelled benzthiophene. Ozonolysis of the benzthiophene (11a) gave the benzazepinone disulfide (13) which was reduced with tributylphosphine to the thiol (4). Direct treatment of the thiol (4) with ethyl bromo-[2-14C]acetate and sodium ethoxide gave the recyclized benzthiophene (14). The ester side chain of 14 was reduced with LAH to give 14C-labeled form of the original starting material. Transformation to 1 was readily accomplished by a manganese dioxide oxidation, Wittig reaction, catalytic reduction sequence.