Premium
Formation of an 6α, 14‐epoxy‐bridged isomorphinan, an unusual product from a substituted 6α,14‐dihydroxymorphinan
Author(s) -
Davis Ronda D.,
Nelson Timothy D.,
Nelson Wendel L.
Publication year - 1994
Publication title -
journal of heterocyclic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.321
H-Index - 59
eISSN - 1943-5193
pISSN - 0022-152X
DOI - 10.1002/jhet.5570310638
Subject(s) - chemistry , alkylation , methylene , epoxide , catalysis , bromide , halide , potassium hydroxide , chloride , ether , phase (matter) , medicinal chemistry , phase transfer catalyst , hydroxide , organic chemistry , polymer chemistry
During alkylation of 3‐ O ‐benzyl‐6α‐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 6α,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 6α‐oxygen displacement of a 14‐ O ‐aralkyl ether intermediate under the phase transfer catalysis alkylation conditions.