Synthesis of S-3-Hydroxyadamantylglycine Ester by a Pd/C Promoted Mild Leuckart-Wallach Reaction and an L-Dibenzoyltartaric Acid Resolution. (February 2015)

• Record Type: Journal Article
• Authors: Pan, Xianhua; Zhao, Dongxian; Shi, Yao; Huang, Youyou; Chen, Siyu; Liu, Feng
• Is Part Of: Journal of chemical research. Volume 39:Number 2(2015)
• Page Start: 108
• Page End: 111
• Publication Date: 2015-02
• Subjects: reductive amination -- α-amino acids -- α-keto acid -- chemical resolution -- L-dibenzoyltartaric acid; Chemistry -- Research -- Periodicals; Chemistry -- Periodicals; 540.5
• DOI: 10.3184/174751915X14227074676509
• Languages: English
• ISSNs: 1747-5198

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.