Abstract
trans-3-Acetyl-4-alkyl pyrrolidin-2-ones 5a, b and 8a, b undergo reductive amination with NaBH 3(CN) in CH 3OH in the presence of CH 3COONH 4. By acylation of the reaction product the corresponding 3-acylaminoethylpyrrolidin-2-ones 9a– c and 10a, b were obtained with total stereoselection. The configuration of the newly formed stereogenic centre at C-1″ of the acylaminoethyl chain was assigned on the basis of 1H NMR data supported by both molecular mechanics and quantomechanical calculations.
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