
TY  - JOUR
A1  - Adams, R 
A1  - Culvenor, CCJ 
A1  - Robinson, CN 
A1  - Stingl, HA 
T1  - Synthesis of Heliotramide
JF  - Australian Journal of Chemistry
JO  - Aust. J. Chem.
Y1  - 1959
VL  - 12
IS  - 4
SP  - 706
EP  - 711
KW  - 
UR  - https://doi.org/10.1071/CH9590706 
N2  - 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. 
ER  -

