Method for preparing alkoxyamine compound by aldehyde reduction and amination

Abstract

The invention discloses a method for preparing an alkoxyamine compound by aldehyde reduction and amination. According to the method, under the water-free and oxygen-free conditions, aldehyde, alkoxyamine hydrochloride, hydrosilane and Lewis acid are added into an organic solvent; reaction is performed under the condition of room temperature to 100 DEG C to obtain the alkoxyamine compound. The hydrosilane is used as a reducing agent; the reaction conditions are mild, green and efficient; under the reaction conditions, N-O bonds in the raw materials cannot fracture; the technical difficulty of completely remaining the alkoxyl groups in products can be effectively solved. Under the nonmetallic catalyst conditions, the metal residue and toxicity problems do not exist.

Description

technical field [0001] The invention relates to a method for preparing alkoxyamine compounds by reacting alkoxyamines with aldehydes under mild conditions in the presence of a hydrogen donor and borane. Background technique [0002] Nitrogen-containing compounds widely exist in nature, and are the structural units of many important biologically active molecules, and are important intermediates for the synthesis of natural products and chiral drugs. Similarly, amine compounds containing alkoxy groups are also one of the important functional groups of molecules with biological activity, and are also widely used in medicine and pesticides. Therefore, the preparation of nitrogen-containing compounds has very important practical significance. [0003] We know that in the synthesis of amine compounds, the reductive amination of aldehydes and ketones is the most direct, effective and commonly used method. The technology of catalytic reduction using hydrogen is very common, but hy...

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Problems solved by technology

The technology of catalytic reduction using hydrogen is very common, but hydrogen as a reducing agent requires a high-pressure device, and the production cost is high and technically complicated (V.A.Tarasevich, N.G.Kozlv, Ruiss.Chem.Rev.1999,68,p55-72); using metal cyanide Although the reduction reaction of metal hydride reagents such as sodium borohydride and sodium cyanoborohydride has mild reaction conditions, there are also risks of toxicity and explosion (G.W.Gribble, Chem.Soc.Rev.1998, 27, P395-404) ; Lewis acids such as magnesium chloride, zinc chloride, etc. can catalyze the amination reaction of carbonyl compounds, but need 150~200 ℃ of high temperature reaction conditions (J.F.Bunnett, J.L.Marks, J.Am.Chem.Soc.1949,71, P1587- 1589); and the reaction of preparing alkoxyl amination by direct reduction of the C=N double bond of oxime is usually difficult to keep alkoxy group or requires harsh hydrogenation reaction conditions (A.Melman in The Chemistry of Hydroxylamines, Oximes and Hydroxamic Acids, Part 1, Wiley, Chichester, 2009, 117-161; J. Mohr and M. Oestreich, Angew. Chem. Int. Ed. 2014, 53, 1-5)

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