An unexpected ring formation in morphine chemistry

Autor(en)

Wilhelm Fleischhacker, Bernd Richter, Gerald Giester, Thomas H. Brehmer

Abstrakt

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(en)

Institut für Mineralogie und Kristallographie

Journal

ARKIVOC

Seiten

82-94

Anzahl der Seiten

13

ISSN

1551-7004

DOI

https://doi.org/10.3998/ark.5550190.0002.210

Publikationsdatum

2001

Peer-reviewed

Ja

ÖFOS 2012

1051 Geologie, Mineralogie

Link zum Portal

https://ucrisportal.univie.ac.at/de/publications/35011979-f6f6-415e-8541-8ccb50a311fe