STEREOCHEMICAL STUDIES:I. CONFIGURATIONS OF SOME 4-AZACHOLESTANES
- 1 August 1960
- journal article
- Published by Canadian Science Publishing in Canadian Journal of Chemistry
- Vol. 38 (8) , 1316-1324
- https://doi.org/10.1139/v60-185
Abstract
The Beckmann rearrangement of the oxime of A-nor-5β-cholestan-3-one gave 4-aza-5β-cholestan-3-one; the isomeric lactam obtained by the reduction of the oxime of 5-oxo-3,5-seco-A-norcholestan-3-oic acid with sodium in alcohol must consequently be 4-aza-5α-cholestan-3-one. Other methods of reducing the oximino acid afforded hydroxamic acids. 4-Aza-5α- and 4-aza-5β-cholestane were obtained by reduction of the appropriate lactam or hydroxamic acid.Keywords
This publication has 7 references indexed in Scilit:
- Leuckart Reduction of Cholestan-3-oneJournal of the American Chemical Society, 1958
- Imine-Enamine Systems and the Mechanism of their Oxidation1Journal of the American Chemical Society, 1956
- Aza-Steroide. II. Synthese der A-Azacholan-Derivate. (2)Pharmaceutical Bulletin, 1955
- Über Steroide und Sexualhormone. 208. Mitteilung. Versuche zur Einführung funktioneller Gruppen in die Stellung 18 des Steroid‐Gerüstes. IIHelvetica Chimica Acta, 1955
- Application of the Favorskii Rearrangement to the Preparation of A-NorsteroidsJournal of the American Chemical Society, 1954
- Studies in Steroid Metabolism. VIII. The Detection and Location of Ethylenic Double Bonds in Steroids by Infrared SpectrometryJournal of the American Chemical Society, 1950
- Ueber CholesterinEuropean Journal of Inorganic Chemistry, 1906