Efficient dynamic kinetic resolution method for the synthesis of enantiopure 6-hydroxy- and 6-methoxy-1,2,3,4-tetrahydroisoquinoline-1-carboxylic acid
Abstract Enantiomeric 6-hydroxy-1,2,3,4-tetrahydroisoquinoline-1-carboxylic acid (ee >99%), useful in the synthesis of modulators of nuclear receptors, including liver X receptor and its analogue 6-methoxy-1,2,3,4-tetrahydroisoquinoline-1-carboxylic acid (ee >99%), a source of the above enanti...
| Published in: | Tetrahedron: Asymmetry |
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| Main Authors: | , , , |
| Format: | Article in Journal/Newspaper |
| Language: | English |
| Published: |
2016
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| Subjects: | |
| Online Access: | http://publicatio.bibl.u-szeged.hu/10568/ http://publicatio.bibl.u-szeged.hu/10568/1/forro_tet.pdf https://doi.org/10.1016/j.tetasy.2016.10.011 |
| Summary: | Abstract Enantiomeric 6-hydroxy-1,2,3,4-tetrahydroisoquinoline-1-carboxylic acid (ee >99%), useful in the synthesis of modulators of nuclear receptors, including liver X receptor and its analogue 6-methoxy-1,2,3,4-tetrahydroisoquinoline-1-carboxylic acid (ee >99%), a source of the above enantiomer was synthesized through Candida antarctica lipase B-catalysed dynamic kinetic hydrolysis of the corresponding 1,2,3,4-tetrahydroisoquinoline-1-carboxylic esters (±)-4·HCl and (±)-5. (R)-Selective hydrolysis in both organic solvents and an aqueous NH4OAc buffer at pH 8.5 was observed and the amino acids were obtained in good chemical yields (>87%). |
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