Chemical and Pharmaceutical Bulletin p. 1995 - 1997 (1995)
Update date:2022-08-11
Topics:
Lee
Eibler
Mayer
Wiegrebe
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.
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