An unexpected ring formation in morphine chemistry
- Author(s)
- Wilhelm Fleischhacker, Bernd Richter, Gerald Giester, Thomas H. Brehmer
- Abstract
Reaction of (7R)-N-benzyl-N-nor-7-bromoneopinone dimethyl acetal (2) with primary or secondary amines (RNH2, R1R2NH) resulted in 9-amino-substituted hasubanan derivatives; in particular, modification of the 9-(2-hydroxyethyl)amino derivative in subsequent steps gave products 8 with a 9-(oxazolidin-2'-one-3'-yl) substituent. 1H and 13C NMR spectra did not provide definitive evidence for the supposed structure and reaction mechanism, but X-ray analyses of compounds 8a and 8d confirmed both structures.
- Organisation(s)
- Department of Mineralogy and Crystallography
- Journal
- ARKIVOC
- Pages
- 82-94
- No. of pages
- 13
- ISSN
- 1551-7004
- DOI
- https://doi.org/10.3998/ark.5550190.0002.210
- Publication date
- 2001
- Peer reviewed
- Yes
- Austrian Fields of Science 2012
- 1051 Geology, Mineralogy
- Portal url
- https://ucrisportal.univie.ac.at/en/publications/an-unexpected-ring-formation-in-morphine-chemistry(35011979-f6f6-415e-8541-8ccb50a311fe).html