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CATALYTIC REDUCTION OF 3-(4,4-DIMETHYL-5-KETO-3-ISOXAZOLE)PROPIONIC ACID AND ITS DERIVATES
Feuer, Henry,Scholl, Philip C.
, p. 29 - 35 (2007/10/02)
Catalytic hydrogenation of 3-(4,4-dimethyl-5-keto-3-isoxazole)propionic acid (1) in glacial acetic acid in the presence of 5percent palladium on charcoal gives 4-amino-5-methylhexanoic acid (2).Reductions of the corresponding esters, methyl 3-(4,4-dimethyl-5-keto-3-isoxazole)propionate (3) and amide, 3-(4,4-dimethyl-5-keto-3-isoxazole)propionamide (4) afford, however, γ-isopropylbutyrolactam (5).Reductions of 1 and 3 in aqueous acetic acid give 4-keto-5-methylhexanoic acid (6) and methyl 4-keto-5-methylhexanoate (7), respectively.On the other hand amide 4 is converted to2-hydroxy-5-isopropylidene-Δ1-pyrroline (8).Compound 8 is also obtained if 4 is reduced in acetic acid containing a small amount of hydrogen chloride.
