Abstract
A mild Leuckart-Wallach reaction in the presence of catalytic amount Pd/C was developed. Under the optimised reaction conditions, 30% Pd/C loading, 40 °C, 6 atm N2 atmosphere, racemic 3-hydroxyadamantylglycine ester was obtained in 85% yield. The racemic amino esters were resolved chemically. The ethyl ester was resolved with L-dibenzoyltartaric acid in i-PrOH, give (S)-3-hydroxyadamantylglycine ester in 99% ee and 34% yield. The enantiomerically enriched unwanted isomer was converted to the racemic amino ester and resolved again.
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