Amarjit Singh, James B. Falabella, T. Laporte
Jul 7, 2015
Citations
2
Influential Citations
8
Citations
Journal
Organic Process Research & Development
Abstract
Lipase PS 30 (immobilized on polypropylene) from Pseudomonas cepacia was used for enantioselective esterification of (RS)-1-(2-fluoro-4-iodophenyl)-3-hydroxypyrrolidin-2-one by using succinic anhydride and 2-methyltetrahydrofuran at 4 °C. The isolation of desired alcohol avoided use of column chromatography, a simple solvent extraction of undesired (R)-4-((1-(2-fluoro-4-iodophenyl)-2-oxopyrrolidin-3-yl)oxy)-4-oxobutanoic acid into 5% potassium bicarbonate solution separated pure desired (S)-1-(2-fluoro-4-iodophenyl)-3-hydroxypyrrolidin-2-one into the 2-methyltetrahydrofuran solution. The reaction conditions were optimized, and (S)-1-(2-fluoro-4-iodophenyl)-3-hydroxypyrrolidin-2-one was prepared in high enantiomeric excess >99% and yield ∼40% (theoretically possible yield 50%). Novozym 435 (Candida antarctica lipase B) was found to be a suitable biocatalyst for the resolution of (RS)-1-(6-bromo-2-methylpyridin-3-yl)-2-oxopyrrolidin-3-yl acetate to form the undesired S-acetate and the desired R-alcohol. The...