
%0 Journal Article
%A Adams, R 
%A Culvenor, CCJ 
%A Robinson, CN 
%A Stingl, HA 
%T Synthesis of Heliotramide
%J Australian Journal of Chemistry
%D 1959/12/01
%V 12
%N 4
%P 706-711
%K 
%R https://doi.org/10.1071/CH9590706
%U https://www.publish.csiro.au/paper/CH9590706 
%X Both racemates of 4-methoxy-3-hydroxy-2-methylpentane-3-carboxamide are synthesized by reacting isopropylmagnesium chloride with 2-methoxypropionitrile, converting the resulting ketone into the cyanohydrin and hydrolysing to the amide. Comparison with heliotramide shows that the lower melting racemate, m.p. 81-82 °C, is (±)-heliotramide and thus of threo-configuration. The higher melting racemate, m.p. 145-146 °C, is the erythro-amide. Attempts to hydrolyse the amides to the carboxylic acids were unsuccessful.   Heliotramide is prepared by heating heliotric acid with urea or by the usual acid chloride-ammonia procedure following protection of the hydroxyl group. 
