Hubei Province Engineering and Technology Research Center for Fluorinated Pharmaceuticals, School of Pharmaceutical Sciences, Wuhan University, Wuhan 430071, China.
State Key Laboratory of Magnetic Resonance and Atomic and Molecular Physics, National Center for Magnetic Resonance in Wuhan, Wuhan Institute of Physics and Mathematics, Innovation Academy of Precision Measurement Science and Technology, Chinese Academy of Sciences, Wuhan 430071, China.
Org Biomol Chem. 2022 Jun 29;20(25):5129-5138. doi: 10.1039/d2ob00605g.
Monodisperse oligoethylene glycols (M-OEGs)-containing symmetrical secondary amines are highly valuable synthetic intermediates in drug development and materials sciences. Scalable three-step synthesis of M-OEGs secondary amines with flexible M-OEGs and/or alkyl chains is described herein. Through reduction amination of diethanolamine, Williamson ether synthesis, and subsequent deprotection, a series of M-OEGs secondary amines with diverse and fine-tunable chemical structures were conveniently prepared. The presented strategy is attractive with readily available starting materials, simple catalytic systems, scalable synthesis, and avoids the use of explosive sodium azide.
含有单分散性聚乙二醇（M-OEG）的对称仲胺是药物开发和材料科学中非常有价值的合成中间体。本文描述了一种可扩展的三步法合成具有灵活的 M-OEG 和/或烷基链的 M-OEG 仲胺。通过二乙醇胺的还原胺化、Williamson 醚合成和随后的脱保护，方便地制备了一系列具有不同和精细可调化学结构的 M-OEG 仲胺。该策略具有吸引力，因为它使用了易于获得的起始原料、简单的催化体系、可扩展的合成方法，并且避免了使用易爆的叠氮化钠。
