1139884-44-8Relevant articles and documents
Microwave-assisted protection of primary amines as 2,5-dimethylpyrroles and their orthogonal deprotection
Walia, Amit,Kang, Soosung,Silverman, Richard B
, p. 10931 - 10937 (2013)
Primary amines can be readily doubly protected as N-substituted 2,5-dimethylpyrroles. Although this protecting group is stable toward strong bases and nucleophiles, long reaction times are required for both the protection and deprotection steps, generally resulting in low deprotection yields. By employing microwave irradiation, protection and deprotection reaction times are dramatically reduced. Furthermore, deprotection with dilute hydrochloric acid in ethanol increases reaction yields. Diverse deprotection conditions have been developed in conjunction with microwave irradiation, so that protection as an N-substituted 2,5-dimethylpyrrole can be orthogonal to other standard amine protecting groups, such as tert-butyloxycarbonyl (Boc), carbobenzyloxy (Cbz), and 9-fluorenylmethyloxycarbonyl (Fmoc).
A method for the selective protection of aromatic amines in the presence of aliphatic amines
Perron, Valerie,Abbott, Shaun,Moreau, Nancie,Lee, Devin,Penney, Christopher,Zacharie, Boulos
experimental part, p. 283 - 289 (2009/06/25)
A simple and efficient procedure has been developed for the regioselective protection of aromatic amines in the presence of aliphatic amines. The method is general for the preparation of mono-N-Boc, -N-Cbz, -N-Fmoc or -N-Alloc aromatic amines in high yield without affecting the aliphatic amines. This approach is applicable to substituted (aminoalkyl)aniline compounds with different functionalities and was employed to supply gram quantities of the protected aniline product. Georg Thieme Verlag Stuttgart · New York.