Efficient synthesis of 5-(hydroxymethyl)piperazin-2-ones using automatically prepared chiral bromocarboxylic acid and Garner's aldehyde as versatile building blocks. (15th May 2021)

• Record Type: Journal Article
• Authors: Masui, Hisashi; Naito, Kohei; Minoshima, Mai; Kusayanagi, Akira; Yosugi, Sae; Shoji, Mitsuru; Takahashi, Takashi
• Is Part Of: Bioorganic & medicinal chemistry letters. Volume 40(2021)
• Publication Date: 2021-05-15
• Subjects: Piperazione -- Amino acid analogs -- Heterocycles -- Automated synthesis -- α-Bromocarboxylic acid; Bioorganic chemistry -- Periodicals; Pharmaceutical chemistry -- Periodicals; 572
• DOI: 10.1016/j.bmcl.2021.127961
• Languages: English
• ISSNs: 0960-894X

Abstract

Graphical abstract: Abstract: An efficient method for the synthesis of substituted 5-(hydroxymethyl)piperazin-2-ones was established by using an automated synthesis process. Thirteen piperazinones were synthesized from chiral α-bromocarboxylic acids and Garner's aldehyde which were prepared by using our originally developed automated synthesizer, ChemKonzert®. The automated method of synthesizing chiral α-bromocarboxylic acids was efficient and safe because the rate of the dropwise addition of the reagent can be controlled using the automated synthesizer. This method is expected to contribute to the synthesis of pharmaceuticals.