STEREOCHEMICAL ELUCIDATION OF THE REACTION-PRODUCTS OF ALPHA-NARCOTINE WITH ETHYL CHLOROFORMATE

Authors
LEE DU ERBLER E MAYER KK WIEGREBE W
Citation
Du. Lee et al., STEREOCHEMICAL ELUCIDATION OF THE REACTION-PRODUCTS OF ALPHA-NARCOTINE WITH ETHYL CHLOROFORMATE, Chemical and Pharmaceutical Bulletin, 43(11), 1995, pp. 1995-1997
Citations number
10
Categorie Soggetti
Pharmacology & Pharmacy",Chemistry
Journal title
Chemical and Pharmaceutical Bulletin → ACNP
ISSN journal
00092363
Volume
43
Issue
11
Year of publication
1995
Pages
1995 - 1997
Database
ISI
SICI code
0009-2363(1995)43:11<1995:SEOTRO>2.0.ZU;2-I
Abstract
alpha-Narcotine (1) was treated with ethyl chloroformate by refluxing in dichloromethane to afford six products, which were separated by pre parative high-performance liquid chromatography (HPLC), Their stereoch emistry and structures were elucidated, This reaction proceeded initia lly to the chloro-carbamates and successively to the corresponding car binols, In addition, N-desmethyl-N-carbethoxynarcotine (3), found in t he HPLC chromatogram, was identified by direct comparison with synthet ic 3; this compound had caused difficulty in our previous mass spectro metric investigations.