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The synthesis of deuterium enriched erythro-α-methylnorepinephrine and norepinephrine

✍ Scribed by Asher Kalir; Curt Freed; Kenneth L. Melmon; Neal Castagnoli Jr.

Book ID
102900882
Publisher
John Wiley and Sons
Year
1977
Tongue
French
Weight
746 KB
Volume
13
Category
Article
ISSN
0022-2135

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✦ Synopsis

Norepinephrine-dlO,dll deuteriochloride and erythro-amethylnorepinephrine-d6,d7 hydrochloride f o r use as mass spectrometric stable isotope internal standards have been synthesized.

of 3,4-dimethoxyacetophenone provided the corresponding

followed by treatment o f the resulting a-bromoketone w i t h dibenzylamine yielded the a-dibenzylamino derivative o f

bromide cleaved the methyl ether groups and introduced three t o four additional deuterium atoms i n the resulting catechol .

Catalytic hydrogenation gave the desired erythro-a-methynorepinephrine enriched w i t h s i x o r seven deuterium atoms. The Trideuteriomethylation of the 1 i thio derivative Bromi nati on Deuteri um *The following two papers dealing w i t h alternative approaches t o labelled catecholamines appeared a f t e r t h i s study was completed:

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