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An improved synthesis of (3R)-2-(tert-butoxycarbonyl)-7-hydroxy-1,2,3,4-tetrahydroisoquinoline-3- carboxylic acid

Liu, C., Thomas, J., Brieaddy, L., Berrang, B., & Carroll, F. (2008). An improved synthesis of (3R)-2-(tert-butoxycarbonyl)-7-hydroxy-1,2,3,4-tetrahydroisoquinoline-3- carboxylic acid. Synthesis, 2008(6), 856-858. https://doi.org/10.1055/s-2008-1032211

Abstract

An improved synthesis of (3R)-2-(tert-butoxycarbonyl)-7-hydroxy-1,2,3,4-tetrahydroisoquinoline-3-carboxylic acid is described wherein a modified Pictet-Spengler reaction was employed to provide 95% yield of the product with 7% racemization or less. The enantiomeric excess of the final product was improved to 99.4% via recrystallization. The overall yield of this four-step synthesis provides the title compound in 43% starting from D-tyrosine.

10.1055/s-2008-1032211

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