Chemoenzymatic route to β-blockers via 3-hydroxy esters

Add time:07/11/2019    Source:sciencedirect.com

Enantiomerically pure precursors of β-blockers (propranolol, alprenolol and 1-(isopropylamino)-3-p-methoxy-phenoxy-2-propanol) were synthesized. Key step is the lipase-catalyzed kinetic resolution of rac-3-hydroxy esters either by O-acylation using vinyl acetate or by hydrolysis of the ester group. Both approaches were highly enantioselective (> 95 %ee) with E-values > 150 using lipase from Pseudomonas cepacia. The formal synthesis of (−)-(S)-propranolol was developed in subsequent steps.

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