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合成工艺开发 (R) -(+) -1,2-环氧-5-二烯:一个重要的状构建块

Daryl Guthrie¹, John M Saathoff¹, Rajkumar Lalji Sahani¹

¹Medicines for All Institute, Virginia Commonwealth University, Richmond, Virginia 23284-3068, United States.

Organic process research & development

|August 22, 2024

概括

开发了两种可扩展的方法来合成奇拉 (R) - ((+) -1,2-环氧-5-烯. 第二种方法,从 (R) -epichlorohydrin开始,为这种有价值的化学中间体提供更高的产量和纯度.

科学领域:

有机合成有机合成
奇拉化学奇拉化学
过程化学过程化学

背景情况:

性环氧化物的合成对于生产药品和精细化学品至关重要.
(R) -(+) -1,2-环氧-5-烯是一种有价值的性构建块,具有多种合成应用.
需要有效和可扩展的合成路线来满足工业需求.

研究的目的:

开发用于 (R) - ((+)) -1,2-环氧-5-的实用和可扩展的合成策略.
在产量,纯度和可扩展性方面比较两个不同的合成方法.
为了提供一种可靠的方法来生产这种性环氧化物中间体.

主要方法:

方法1:两步合成,使用甲基酸 (mCPBA) 进行环氧化,然后使用 (salen) Co (II) 进行性分离.
方法2:从 (R) -epichlorohydrin开始的两步合成,包括用化 (allylMgCl) 打开环氧化环,然后用NaOH介导环闭.
这两种方法都在100-200克尺度上得到了验证.

主要成果:

方法1产生了 (R) -(+) -1,2-环氧-5-烯,总产量为24-30%.
方法2提供了 (R) -(+) -1,2-环氧-5-烯在55-60%的总分离产量中,具有特殊的纯度.
第二种方法证明了生产合环氧化的高效性和可扩展性.

结论:

已经成功地建立了两个可行的合成路径,用于 (R) - ((+) -1,2-环氧-5-hexene.
使用 (R) -epichlorohydrin 的方法是首选的,因为它的产量和纯度更高.
这些可扩展的工艺为工业生产性环氧化物提供了实际的解决方案.

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