Enzymatic resolution of 5-hydroxy- and 8-hydroxy-2-tetralols using immobilized lipases |
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| Authors: | Paolo Bonomi Paola Cairoli Daniela Ubiali Carlo F Morelli Marco Filice Ines Nieto Massimo Pregnolato Paolo Manitto Marco Terreni Giovanna Speranza |
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| Institution: | 1. Dipartimento di Chimica Organica e Industriale, Università degli Studi di Milano and Italian Biocatalysis Center, via Venezian 21, 20133 Milano, Italy;2. Dipartimento di Chimica Farmaceutica, Pharmaceutical Biocatalysis Laboratories, Università degli Studi di Pavia and Italian Biocatalysis Center, via Taramelli 12, 27100 Pavia, Italy;3. Innovate Biotechnology srl and Italian Biocatalysis Center, Parco Scientifico Tecnologico, Strada Savonesa 9, 15050 Rivalta Scrivia (AL), Italy |
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| Abstract: | (R)-2-Tetralol (R)-2a, (R)-5-hydroxy-2-tetralol (R)-2b and (R)-8-hydroxy-2-tetralol (R)-2c, which are key intermediates in the synthesis of pharmacologically active 2-aminotetralins 3, were prepared in moderate to very high enantiomeric excess (up to 99% ee) by enzymatic resolution of the corresponding racemic butyrates rac-1a, rac-1b and rac-1c, respectively, using lipases immobilized on octyl agarose. This methodology is an alternative to the microbial reduction of 2-tetralones. |
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