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Protection of the allylic alcohol double bond from catalytic reduction in the preparation of [1‐ 3 H]morphine and [1‐ 3 H]codeine
Author(s) -
Seltzman Herbert H.,
Roche Michael J.,
Laudeman Christopher P.,
Wyrick Christopher D.,
Carroll F. Ivy
Publication year - 1998
Publication title -
journal of labelled compounds and radiopharmaceuticals
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.432
H-Index - 47
eISSN - 1099-1344
pISSN - 0362-4803
DOI - 10.1002/(sici)1099-1344(1998090)41:9<811::aid-jlcr132>3.0.co;2-3
Subject(s) - chemistry , codeine , allylic rearrangement , morphine , double bond , alcohol , catalysis , allylic alcohol , aryl , selective reduction , organic chemistry , anesthesia , alkyl , medicine
The t‐butyldimethylsilylation of the allylic alcohol of 1‐iodomorphine and 1‐iodocodeine protects the double bond of these molecules from catalytic reduction while allowing the reduction of the aryl iodide. This selectivity has been applied to the preparation of tritiated morphine and codeine without complicating over reduction to the dihydromorphine and dihydrocodeine. © 1998 John Wiley & Sons, Ltd.