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The synthesis of 13C-enriched α-methyldopa

✍ Scribed by Matthew M. Ames; Neal Castagnoli Jr.

Publisher
John Wiley and Sons
Year
1974
Tongue
French
Weight
393 KB
Volume
10
Category
Article
ISSN
0022-2135

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✦ Synopsis

Abstract

Alpha‐methyldopa hydrochloride, specifically labelled with ^13^C in the benzylic position, was prepared for use in biotransformation studies. Carbonation of the lithio derivative of 3,4‐dibenzyloxybenzene with ^13^CO~2~ (64 atom percent) was followed by LiA1H~4~ reduction of the resulting benzoic acid. Oxidation with CrO~3~ provided the benzaldehyde which was condensed with nitroethane to form the phenylnitropropene, Reduction of this phenylnitropropene with Fe/HOAc gave the corresponding phenyl‐2‐propanone which was converted to its hydantoin derivative. Base hydrolysis of the hydantoin followed by debenzylation in concentrated hydrochloric acid gave the desired alpha‐methyldopa hydrochloride in 16% overall yield.

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