Stereochemical elucidation of the reaction products of α-narcotine with ethyl chloroformate

Article abstract of DOI:10.1248/cpb.43.1995

α-Narcotine (1) was treated with ethyl chloroformate by refluxing in dichloromethane to afford six products, which were separated by preparative high-performance liquid chromatography (HPLC). Their stereochemistry and structures were elucidated. This reaction proceeded initially to the chloro- carbamates and successively to the corresponding carbinols. In addition, N- desmethyl-N-carbethoxynarcotine (3), found in the HPLC chromatogram, was identified by direct comparison with synthetic 3; this compound had caused difficulty in our previous mass spectrometric investigations.

Full text of DOI:10.1248/cpb.43.1995

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