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A scalable synthesis of the (S)-4-(tert-butyl)-2-(pyridin-2-yl)-4,5-dihydrooxazole ((S)-t-BuPyOx) ligand.
Beilstein Journal of Organic Chemistry ( IF 2.2 ) Pub Date : 2013 , DOI: 10.3762/bjoc.9.187
Hideki Shimizu 1 , Jeffrey C Holder , Brian M Stoltz
Affiliation  

An efficient method for the synthesis of the (S)-4-(tert-butyl)-2-(pyridin-2-yl)-4,5-dihydrooxazole ((S)-t-BuPyOx) ligand has been developed. Inconsistent yields and tedious purification in known routes to (S)-t-BuPyOx suggested the need for an efficient, dependable, and scalable synthetic route. Furthermore, a route suitable for the synthesis of PyOx derivatives is desirable. Herein, we describe the development of a three-step route from inexpensive and commercially available picolinic acid. This short procedure is amenable to multi-gram scale synthesis and provides the target ligand in 64% overall yield.

中文翻译:

(S)-4-(叔丁基)-2-(吡啶-2-基)-4,5-二氢恶唑 ((S)-t-BuPyOx) 配体的可扩展合成。

已开发出一种合成 (S)-4-(叔丁基)-2-(吡啶-2-基)-4,5-二氢恶唑 ((S)-t-BuPyOx) 配体的有效方法。在 (S)-t-BuPyOx 的已知路线中不一致的产量和繁琐的纯化表明需要有效、可靠和可扩展的合成路线。此外,需要适合合成 PyOx 衍生物的路线。在此,我们描述了从廉价且市售的吡啶甲酸开发三步路线。这个简短的程序适用于多克规模的合成,并以 64% 的总产率提供目标配体。
更新日期:2017-01-31
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