FORMATION OF AN 6-ALPHA,14-EPOXY-BRIDGED ISOMORPHINAN, AN UNUSUAL PRODUCT FROM A SUBSTITUTED 6-ALPHA,14-DIHYDROXYMORPHINAN

During alkylation of 3-O-benzyl-6alpha-naltrexol (1) with large aralkyl halides like 2-bromomethylnaphthalene and 9-chloromethylanthracene under phase transfer catalysis conditions (potassium hydroxide, tetrabutylammonium bromide, methylene chloride), formation of a new 6alpha,14-epoxide-bridged iso...

Full description

Saved in:
Bibliographic Details
Published inJournal of heterocyclic chemistry Vol. 31; no. 6; pp. 1509 - 1511
Main Authors DAVIS, RD, NELSON, TD, NELSON, WL
Format Journal Article
LanguageEnglish
Published TAMPA HETERO CORPORATION 01.11.1994
Subjects
Chemistry
Chemistry, Organic
Physical Sciences
Science & Technology
Online AccessGet more information

Cover

More Information
Summary:During alkylation of 3-O-benzyl-6alpha-naltrexol (1) with large aralkyl halides like 2-bromomethylnaphthalene and 9-chloromethylanthracene under phase transfer catalysis conditions (potassium hydroxide, tetrabutylammonium bromide, methylene chloride), formation of a new 6alpha,14-epoxide-bridged isomorphinan (4) was noted. Chemical and spectral evidence, including nmr and mass spectral data, are presented to prove its structure. Its formation results from 6alpha-oxygen displacement of a 14-O-aralkyl ether intermediate under the phase transfer catalysis alkylation conditions.
ISSN:0022-152X
DOI:10.1002/jhet.5570310638