89854-70-6Relevant academic research and scientific papers
One-Pot Synthesis of Primary and Secondary Aliphatic Amines via Mild and Selective sp3 C?H Imination
Comito, Robert J.,Ghosh, Subrata K.,Hu, Mengnan
supporting information, p. 17601 - 17608 (2021/11/03)
The direct replacement of sp3 C?H bonds with simple amine units (?NH2) remains synthetically challenging, although primary aliphatic amines are ubiquitous in medicinal chemistry and natural product synthesis. We report a mild and selective protocol for preparing primary and secondary aliphatic amines in a single pot, based on intermolecular sp3 C?H imination. The first C?H imination of diverse alkanes, this method shows useful site-selectivity within substrates bearing multiple sp3 C?H bonds. Furthermore, this reaction tolerates polar functional groups relevant for complex molecule synthesis, highlighted in the synthesis of amine pharmaceuticals and amination of natural products. We characterize a unique C?H imination mechanism based on radical rebound to an iminyl radical, supported by kinetic isotope effects, stereoablation, resubmission, and computational modeling. This work constitutes a selective method for complex amine synthesis and a new mechanistic platform for C?H amination.
Recycling the tert-butanesulfinyl group in the synthesis of amines using tert-butanesulfinamide
Wakayama, Masakazu,Ellman, Jonathan A.
experimental part, p. 2646 - 2650 (2009/08/15)
A practical process for recycling the tert-butanesulfinyl group upon deprotection of N-tert-butanesulfinyl amines has been achieved. Treatment of N-tert-butanesulfinyl amines with HCl in cyclopentyl methyl ether results in complete conversion to tert-butanesulfinyl chloride and the corresponding amine hydrochloride salt, which is isolated by filtration in analytically pure form and in quantitative yield. Treatment of the resulting sulfinyl chloride solution with aqueous ammonia then provides analytically pure tert-butanesulfinamide in 97% yield. Alternatively, the tert-butanesulfinyl chloride solution can be treated with ethanol and catalytic quinidine as a sulfinyl transfer catalyst to provide a cyclopentyl methyl ether solution of ethyl tert-butanesulfinate with 88% ee. Addition of NaNH2 in ammonia followed by simple trituration of the product with octane provides tert-butanesulfinamide with 99% ee and in 67% overall isolated yield based upon the starting N-tert-butanesulfinyl amine.
DICYANOPYRROLIDINES AS DIPEPTIDYL PEPTIDASE IV INHIBITORS
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Page/Page column 30, (2008/06/13)
The invention provides compounds of formula (I), the prodrugs and stereoisomers thereof, and the pharmaceutically acceptable salts of the compounds, prodrugs, and stereoisomers, wherein wherein R is as defined herein; pharmaceutical compositions thereof;
A Simple, One-Pot Transformation of t-Alkyl Chlorides Into (t-Alkyl)amines
Koziara, Anna,Osowska-Pacewicka, Krystyna,Zawadzki, Stefan,Zwierzak, Andrzej
, p. 487 - 489 (2007/10/02)
t-Alkyl chlorides are readily azidated using trimethylsilyl azide in the presence of tin tetrachloride.Tertiary azides can be transformed without isolation into the corresponding (t-alkyl)amine hydrochlorides in a one-pot procedure employing the Staudinger reaction.
