Synthesis of 3H‐etomidate ano resolution into its enantiomers

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Abstract
Etomidate, (R)‐(+)‐ethyl 1‐(1‐phenylethyl)‐1H‐inidazole‐5‐carboxylate, is a short‐acting hypnotic. Tritium was introduced in the ortho‐position of the phenyl‐group by catalytic dehalogenation of the 2‐chloro‐analogue. The homologous tritiated methyester, (+)‐methyl 1‐(1‐phenylethyl)‐1H‐imidazole‐5‐carboxylate, was hydrolyzed to the corresponding carboxylic acid. The resolution into both enantiomers was carried out by successive salt formation with (R)‐(+)‐ and (S)‐(‐)‐α‐methylbenzenemethanamine. After isolation of the diastereoisomeric salts, both enantiomers were obtained by esterification of the salts in ethanol, saturated with HCl‐gas.

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