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Apomorphinans from Isoquinolines: Grewe cyclization of 1‐(2‐hydroxybenzyl)‐ N ‐methyloctahydroisoquinoline and its O ‐methyl ether
Author(s) -
Schmidhammer Helmut,
Brossi Arnold,
FlippenAnderson Judith L.,
Gilardi Richard
Publication year - 1983
Publication title -
helvetica chimica acta
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.74
H-Index - 82
eISSN - 1522-2675
pISSN - 0018-019X
DOI - 10.1002/hlca.19830660807
Subject(s) - chemistry , hydrobromide , isoquinoline , hydrobromic acid , ether , medicinal chemistry , optically active , amine gas treating , salt (chemistry) , organic chemistry
Wolff ‐ Kishner reduction of the optically active ketomorphinan 5 afforded the optically active morphinan 6 differing chromatographically and spectroscopically from the material obtained in a Grewe ‐cyclization of the isoquinoline 1 . A single crystal X‐ray analysis of a hydrobromide salt of a phenolic amine obtained from 1 and 2 with refluxing hydrobromic acid showed this compound to be the N ‐methylapomorphinan 4 .