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Paper | Regular issue | Vol 45, No. 12, 1997, pp.2405-2412
Published online, 1st January, 1970
DOI: 10.3987/COM-97-7977
New Route to 7a-Angularly Substituted Hydroindoles

Kunihiko Mohri,* Yuki Yoshida, Shin-ichiro Mataga, Yohko Hisatsune, Kimiaki Isobe, and Yoshisuke Tsuda

*Showa Pharmaceutical University, 3-3165, Higashi-tamagawagakuen, Machida, Tokyo 194-8543, Japan

Abstract

Strecker type reaction of ethyl 2-oxocyclohexaneacetate with sodium cyanide and ammonium acetate gave 7a-cyano-octahydro-cis-1H-indol-2-one (2a) as a single product, which was alkylated to the N-alkyl derivatives. The cyano group in 2a was convertible to ethoxycarbonylmethyl group by reaction with the Reformatsky reagent generated from ethyl bromoacetate. In the case of the N-methyl derivative 2b, the cyano group was transformed into ethoxycarbonylacetyl group under the same reaction conditions.