Selective Synthesis of 3-bulkyalkylsubstituted 5-aminoisoxazol
(1993) Societes Chimiques Belges. Bulletin —
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- Methyl 2-ethylbutyrate (3) plus lithiumdiisopropylamide reacted with methyl iodide to give methyl 2-ethyl-2-methylbutyrate (4). The methylene carbanion of acetonitrile -generated with lithiumdiisopropylamide- reacted with 4 to give 4-ethyl-4-methyl-3-oxohexanenitrile (5). 3-Ketonitrile 5 reacted with hydroxylamine after 20 min of heating to reflux in ethanol to give 4-ethyl-4-methyl-3-oxohexanitrile oxime (6). This in aqueous dilute HCl was selectively and quantitatively transformed into 5-amino-3 (1-ethyl-1-methylpropyl)isoxazol (7). Longer heating of 5 with hydroxylamine directly generated a mixture of 7 with its isomer 3-amino-5-(1-ethyl-1-methylpropyl)isoxazol (7b). Reaction conditions were studied for optimization of the 5-aminoisoxazol 7 synthesis.
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Rouchaud, J., Gustin, F., & Moulard, C. (1993). Selective Synthesis of 3-bulkyalkylsubstituted 5-aminoisoxazol. Societes Chimiques Belges. Bulletin. https://doi.org/10.1002/bscb.19931020807