Berger, Kathleen J.; Driscoll, Julia L.; Yuan, Mingbin; Dherange, Balu D.; Gutierrez, Osvaldo; Levin, Mark D. published their research in Journal of the American Chemical Society in 2021. The article was titled 《Direct Deamination of Primary Amines via Isodiazene Intermediates》.Name: tert-Butyl 4-aminopiperidine-1-carboxylate The article contains the following contents:
A reaction that selectively deaminated primary amines and anilines under mild conditions and with remarkable functional group tolerance including a range of pharmaceutical compounds, amino acids, amino sugars, and natural products was reported. An anomeric amide reagent was uniquely capable of facilitating the reaction through the intermediacy of an unprecedented monosubstituted isodiazene intermediate. In addition to dramatically simplifying deamination compared to existing protocols, this approach enabled strategic applications of iminium and amine-directed chemistries as traceless methods. Mechanistic and computational studies supported the intermedicacy of a primary isodiazene which exhibited an unexpected divergence from previously studied secondary isodiazenes, leading to cage-escaping, free radical species that engage in a chain, hydrogen-atom transfer process involving aliphatic and diazenyl radical intermediates. In the experimental materials used by the author, we found tert-Butyl 4-aminopiperidine-1-carboxylate(cas: 87120-72-7Name: tert-Butyl 4-aminopiperidine-1-carboxylate)
tert-Butyl 4-aminopiperidine-1-carboxylate(cas: 87120-72-7) belongs to anime. Many important products require amines as part of their syntheses. Methylamine is utilized in the production of the analgesic meperidine (trade name Demerol) and the photographic developer Metol (trademark), and dimethylamine is used in the synthesis of the antihistamine diphenhydramine (trade name Benadryl), the solvent dimethylformamide (DMF), and the rocket propellant 1,1-dimethylhydrazine. The synthesis of the insect repellent N,N-diethyl-m-toluamide (DEET) incorporates diethylamine while that of the synthetic fibre Kevlar requires aromatic amines.Name: tert-Butyl 4-aminopiperidine-1-carboxylate
Referemce:
Piperidine – Wikipedia,
Piperidine | C5H11N – PubChem