Premium
Synthesis of morphine‐d 5 and codeine‐d 8
Author(s) -
Lawson John A.,
DeGraw Joseph I.,
Anbar Michael
Publication year - 1976
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.5570130334
Subject(s) - chemistry , codeine , morphine , tetrahydrofuran , deuterium , demethylation , sodium , lithium (medication) , organic chemistry , pharmacology , medicine , biochemistry , physics , gene expression , quantum mechanics , solvent , dna methylation , gene , endocrinology
The synthesis of morphine labeled with deuterium in the N ‐methyl group and at positions 1 and 6 is described. Reduction of N ‐carboethoxy‐1‐bromonorcodeinone (IV) with lithium aluminum deuteride in tetrahydrofuran‐d 5 yielded the codeine‐d 5 . O‐Demethylation with sodium propylmercaptide‐dimethyl formamide afforded morphine‐d 5 , which could be remethylated with perdeuterioiodomethane to give codeine‐d 8 . The labeled compounds are useful as standards for field ionization mass spectrometric analysis.