2-Pyridone → HCID 11781538, compound

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Reaction Steps

Pyridinone derivative (R) can be reduced to form pyridinone derivative (T) as shown in Reaction Scheme X. A similar result in Reaction Scheme X can be obtained for the corresponding derivative of pyridinone (E). wherein Z, R2, R3, and R4 are as defined in Reaction Scheme VI. The reduction of the nitrile substituted pyridinone derivative (R) is accomplished by combining PtO2 and the nitrile substituted pyridinone in dry ethanol and adding CHCl3. The combined reaction mixture is agitated under hydrogen pressure at room temperature for about 24 hours. The preparation of pyridinone derivative (T) is illustrated by a procedure described by Clive D. L. J., Hisaindee, S., J. Org. Chem. 2000, 65: 4923-4929 in their synthesis of racemic brevioxime and related model compounds, the entirety of which is hereby incorporated by reference. The authors describe the preparation of 3-[[Dimethyl(1,1-dimethylethyl)silyl]oxy]-4,4-dimethoxybutanamine Hydrochloride from 3-[[Dimethyl(1,1-dimethylethyl)silyl]oxy]-4,4-dimethoxybutanenitrile. A solution of 3-[[Dimethyl(1,1-dimethylethyl)silyl]oxy]-4,4-dimethoxybutanenitrile in dry ethanol was added to a suspension of Adam's catalyst in dry ethanol, followed by the addition of bench CHCl3. The mixture was shaken under hydrogen at room temperature for 24 hours. The catalyst was filtered off and the filtrate was evaporated. The residue was kept under oil pump vacuum for 24 hours to give 3-[[Dimethyl(1,1-dimethylethyl)silyl]oxy]-4,4-dimethoxybutanamine.

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