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Two Scalable Syntheses of 3-(Trifluoromethyl)cyclobutane-1-carboxylic Acid
Organic Process Research & Development ( IF 3.1 ) Pub Date : 2020-12-21 , DOI: 10.1021/acs.oprd.0c00422
Zhiguo J. Song 1 , Ji Qi 1 , Marion H. Emmert 1 , Jinxing Wang 2 , Xuezhi Yang 2 , Dong Xiao 3
Affiliation  

Two efficient synthetic methods for preparation of 3-(trifluoromethyl)cyclobutane-1-carboxylic acid are reported starting from readily available 4-oxocyclobutane precursors. These cyclobutanones can be converted to their CF3 carbinols upon treatment with TMSCF3 and a fluoride source. The bis-carboxylate system 9 was deoxygenated by treatment of Bu3SnH and provided desired compound 1 upon decarboxylation. In the monocarboxylate system 15, the triflate could be efficiently eliminated; subsequent hydrogenation afforded cis-1.

中文翻译:

3-(三氟甲基)环丁烷-1-羧酸的两个可扩展合成

从容易获得的4-氧代环丁烷前体开始,报道了两种用于制备3-(三氟甲基)环丁烷-1-羧酸的有效合成方法。这些环丁酮可以在用TMSCF 3和氟化物源处理后转化为CF 3甲醇。通过Bu 3 SnH的处理使双羧酸酯体系9脱氧,并在脱羧后提供所需的化合物1。在单羧酸盐体系15中,可以有效地消除三氟甲磺酸盐;随后的氢化,得到顺式- 1
更新日期:2021-01-16
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