Journal of Organic Chemistry p. 2033 - 2036 (1987)
Update date:2022-07-29
Topics:
Hoegberg, Thomas
Stroem, Peter
Ebner, Michael
Raemsby, Sten
Cyanide anion was found to be a versatile catalyst in the aminolysis of nonactivated esters.A comparative study on various catalysts, including (dimethylamino)pyridine, 2-hydroxypyridine, imidazole, and sodium cyanide, in the ammonolysis of ethyl (S)-1-ethyl-2-pyrrolidinecarboxylate (1) in methanol showed sodium cyanide to be the superior catalyst.Furthermore, the reaction was completely stereoconservative; i.e., less than 1percent racemization occurred.Cyanide ion also proved to be an efficient catalyst in the transesterification with the solvent.Comparative studies on 1, ethyl benzoate (4), ethyl 3-phenylpropionate (5), and ethyl phenoxyacetate (6) in aminolysis with ammonia, methylamine, and dimethylamine in methanol showed cyanide to be a general catalyst.The reactivity order for various esters was found to be MeNH2 > NH3 > Me2NH.
View MoreShandong Yuanli Science and Technology Co., Ltd.
Contact:86-0536-6777557
Address:Zhuliu Industiral Park,Changle County
Hangzhou Think Chemical Co. Ltd
website:http://www.thinkchem.com/
Contact:86-571-89986307/81956191/81956084/81956192
Address:Room 501-502, Tower E, Yuanjian Building, Yuanyang International Center, Hangzhou-310011, China
website:http://www.amadischem.com
Contact:86-571-89925085
Address:Watts Cosine.No.166.Xiangmao Road.
Yangzhou Zhongbao Pharmaceutical Co.,Ltd
Contact:+86-514-88290838
Address:Jiangsu Baoying county economic develpment zone in baoying avenue91
Shandong Xiangde Biotechnology Co., Ltd
Contact:+86 -15066639877
Address:Sanba street
Doi:10.1016/j.jorganchem.2005.09.022
(2006)Doi:10.1002/hlca.200890206
(2008)Doi:10.1039/c4cc05724d
(2014)Doi:10.1016/S0040-4039(00)84689-4
(1986)Doi:10.1007/BF01175056
(1986)Doi:10.1021/ja025608h
(2002)