Ketones Methoxyamine

Ketones may also be converted into amines, if they are first reacted with ammonium salts ot methoxyamine and then reduced with sodium trihydrocyanoborate at pH 7, where carbonyl groups are not attacked (M.-H. Boutigue, 1973). 

Lithium aluminum hydride-Hexa-methylphosphoric triamide, 159 Methoxyamine, 177 Titanium(III) chloride-Diisobutyl-aluminum hydride, 303 Trimethylsilyl chlorochromate, 327 From vinylsilanes m-Chloroperbenzoic acid, 76 Miscellaneous methods to prepare ketones... 

On treatment of cyclopropanecarbaldehydes and cyclopropyl ketones with hy-droxylamine, ° methoxyamine, semicar-bazide ° and amines,the corresponding oximes, O-methyl-oximes, semicarbazones, and imines, respectively, were obtained, often in excellent yield. For example, formation of imine 4. Vicinal primary diamines may react with both amino... 

Treatment of 11 with methoxyamine hydrochloride in pyridine afforded the oxime 23, which was oxidized with chromium trioxide in pyridine to afford the ketone 24 (Scheme... 

USE Analytical reagent for aldehydes and ketones. The addition of methoxyamine to a,ft-unsaturated ketones and the rearrangement of 6 -methoxyamino ketones is described... 

Methoxyamine solid supports 7x can be used to anchor carboxylic acids in the presence of BOP/DIEA as Weinreb amides [338,339]. The resultant anchor is compatible with peptide assembly using Boc or Fmoc strategies, and treatment of the final sequence with LiAlH4 in THF led to release of peptide aldehydes. A related support with RAM as the base resin has also been used to prepare resin-bound Weinreb amides, which afforded ketones on cleavage induced by reaction with Grignard reagents [340]. 

Methoxyimino-ketones are not only variants of the 1,3-dicarbonyl group, but also they have the advantage of affording excellent regioselectivity for the pyrazole formation. Chemoselective condensation between the diketoester and methoxyamine hydrochloride produced... 

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