Scaling-Up
of “Smart Cosubstrate” 1,4-Butanediol
Promoted Asymmetric Reduction of Ethyl-4,4,4-trifluoroacetoacetate
in Organic Media
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Abstract
Biocatalytic asymmetric reduction
of ethyl-4,4,4-trifluoroacetoacetate
under water-deficient reaction conditions using a “smart cosubstrate”
1,4-butanediol was demonstrated up to a 2 L scale. Substrate concentrations
of 100 g/L were applied by using half-molar equivalent of 1,4-butanediol
in methyl-<i>tert</i>-butylether (MTBE). Using this approach,
full conversion of ethyl-4,4,4-trifluoroacetoacetate to the corresponding
(<i>S</i>)-alcohol with an excellent enantiomeric excess
(ee) of ≥99% was accomplished in 5 days. 150 g of isolated
enantiopure product with high purity (94%) was obtained