A new synthetic route for the preparation of pregabalin. Issue 13 (3rd July 2021)

• Record Type: Journal Article
• Authors: He, Chasheng; Zhai, Ziran; Zhou, Yang; Li, Jianqi; Wang, Guan
• Is Part Of: Synthetic communications. Volume 51:Issue 13(2021)
• Page Start: 2034
• Page End: 2040
• Publication Date: 2021-07-03
• Subjects: Cyanide reagent -- Michael addition -- oxaoxazolidinone -- pregabalin -- recrystallization; Organic compounds -- Synthesis -- Periodicals; Chemistry, Organic; Synthesis; 547.205
• DOI: 10.1080/00397911.2021.1919710
• Languages: English
• ISSNs: 0039-7911

Abstract

Abstract: We reported the synthesis of (S)-pregabalin in a five-step sequence with 20% overall yield. As a modification of the previously developed route, a Michael addition between CH3 NO2 and chiral oxaoxazolidinone was employed as a key operation for introducing the methyleneamino group, which allowed avoiding the use of toxic cyanide reagent and led to enantiomerically pure product (>99% ee) after the recrystallization in appropriate solvent. Graphical Abstract: UF0001