The use of methoxy acetoxy esters significantly enhances reaction rates in the lipase-catalyzed preparation of enantiopure 1-(4-chloro phenyl) ethyl amines

Add time:07/15/2019    Source:sciencedirect.com

In this paper we report on the lipase-catalyzed preparation of enantiopure amines. Hydrolysis of two different (R,S)-[1-(4-chlorophenyl)] ethyl amides was best performed in phosphate buffer, resulting in conversions ∼48% and optical purities of the (S)-product >99% ee. Similar optical purities and conversions were found in the R-selective acylation of the (R,S)-amine using two different acyl donors in t-butylmethyl ether. The reaction rate was significantly enhanced using methoxy acetoxy acid derivatives either as leaving group in the hydrolysis of the (R,S)-amide or as ethyl ester in the acylation of the (R,S)-amine. In all reactions studied, immobilized lipase from Candida antarctica B gave the best results.

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