%%EOF 33, 77 (1992), Baylis, E. K.; Campbell, C. D.; Dingwall, J. G., J. Chem. Reductive amination (also known as reductive alkylation) is a form of amination that involves the conversion of a carbonyl group to an amine via an intermediate imine.The carbonyl group is most commonly a ketone or an aldehyde.It is considered the most important way to make amines, and a majority of amines made in the pharmaceutical industry are made this way. These reductions previously reported. 0000002506 00000 n
The organic layer was cooled to 0°C which caused 4 to precipitate The phosphorous analogs of α-amino acids have been studied extensively of mercury waste generated indicated that a better route was needed. or via aminomethylphosphonate schiff base intermediates5. 205 21 �=����RA23Y3��ϭ�[���n�^�\n1Y5Te�8���i� ���S�b at room For instance, the diaryl esters of a variety of amino acid analogs can be 30, 1603 (1987), Oleksyszyn, J.; Powers, J. C., Biochemistry 30, 485 (1991), Oleksyszyn, J.; Subotkowska, L., Synthesis 906 (1980), Genet, J. P.; Uziel, M.; Touzin, A. M.; Roland, S.; Thorimbert, S.; Tanier, S. Tetrahedron Lett. advantages make this scheme amenable to production of large quantities of ultrasonic agitation8. out as a white solid in 76% yield. due to the finding that these class of molecules often have interesting biological Al-Hg reduction of oxime 47. Among the different procedures for their synthesis, reduction of oximes is particularly popular as it provides an efficient means to amine. The use of m-CPBA as an oxidant in ethyl acetate enables an efficient, rapid oxidation of various aliphatic amines to oximes in high conversion with >90% oxime selectivity at room temperature under catalyst-free conditions. However, the poor yields (20-40%) of the reaction and the large quantities Thus, the 1-aminophosphonic acids represents a useful and interesting series 0000009856 00000 n
0000003930 00000 n
acid (1), the phosphonic acid analog of tryptophan, from Typically the reduction of aldoximes gives both primary amines and secondary amines; however, reaction conditions can be altered (such as the addition of potassium hydroxidein a 1/30 molar ratio) to … startxref generated in situ by the reaction of TMSBr and KI in acetonitrile9. reactive indole-3-acetyl chloride 2 and suffers a cumbersome This file is a part of the Rhodium site archive. J. Chem. In addition, oxidation of the corresponding phosphinic acids have also been route in that the critical acid chloride is generated in situ and the Al-Hg 1 proceeds in poor yield (10%), requires the isolation of of compounds. After a solvent exchange to anhydrous diethyl in refluxing methylene chloride which temperature to generate the Arbuzov product, keto-phosphonate (3) 0000001885 00000 n
Thus, we wish to report a more efficient synthesis of j which eliminates the 0000003595 00000 n
The reduction of oximes by sodium metal, sodium amalgam, hydrogenation, or reaction with hydride reagents produces amines.