Product Details of 177-11-7. Trillo, P; Adolfsson, H in [Trillo, Paz; Adolfsson, Hans] Umea Univ, Dept Chem, KBC3,Linnaeus Vag 10, SE-90187 Umea, Sweden published Direct Catalytic Reductive N-Alkylation of Amines with Carboxylic Acids: Chemoselective Enannine Formation and further Functionalizations in 2019, Cited 66. The Name is 1,4-Dioxa-8-azaspiro[4.5]decane. Through research, I have a further understanding and discovery of 177-11-7.
Direct reductive N-alkylation of secondary amines with carboxylic acids using molybdenum hexacarbonyl (5 mol %) as catalyst and diethoxymethylsilane as reducing agent generate enamines in a straightforward fashion in high yields. The formed enamines are without the need for isolation or purification further reacted with trimethylsilyl cyanide in the same reaction flask to yield alpha-amino nitriles in good yields. In the optimized reaction conditions equimolar amounts of carboxylic acid and amine are reacted under neat conditions, and a catalytic amount of trifluoroethanol (0.1 mol %) is added along with TMSCN for the cyanation step. The reductive N-alkylation reaction is demonstrated to be highly chemoselective, tolerating a multitude of different functional groups present in the starting carboxylic acids and amines. The reaction is scalable and the generated alpha-amino nitriles are converted to other useful compounds, e.g., alpha-amino acids or amino-tetrazoles. In addition, the intermediate enamines are further transformed into triazolines, sulfonylformamidines, pyrimidinediones, and TMS-propargylamines, respectively, in high yields under mild reaction conditions. Benzoic acids react with secondary amines under similar conditions to give tertiary amines in high yields, and using this methodology, the biologically active compound Piribedil was isolated in 80% yield in a direct one-pot reaction setup.
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