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Catalytic Reduction of 3-(4,4-Dimethyl-5-keto-3-isoxazole)propionic Acid and Its Derivatives

1982; Elsevier BV; Volume: 18; Issue: 1 Linguagem: Inglês

10.3987/s(b)-1982-01-0029

1881-0942

Paul J. Gilligan, Henry Feuer, Philip C. Scholl,

Synthesis and Characterization of Heterocyclic Compounds

Deceased-Catalytic hydrogenation o f 3-(4.4-dimethyl-5-keto-3-isoxazole)propionicacid (Ji) i n g l a c i a l acetic acid i n the presence o f 5% p a l l adium on charcoal gives 4-amino-5-methylhexanoic acid (2).Reductions o f the corresponding ester.methyl 3-(4.4-dimethyl-5-keto-3-isoxazo1e)propionate(2) and amide.3-(4.4-dimethyl-5-keto-3-isoxazo1e)propionamide(a) afford.however, r-isopropylbutyrolactam (2).Reductions of & and 2 i n aqueous acetic acid give 4-keto-5-methylhexanoic acid (t) and methyl 4-keto-5-methylhexanoate ( l ) , respectively.On the other hand amide i s converted t o Z-hydroxy-5- 1 isopropylidene-A -pyrroline ($1.Compound $ i s also obtained i f $ i s reduced i n acetic acid containing a small amount of hydrogen chloride.Syntheses of 3-(4.4-dimethyl-5-keto-3-isoxazo1e)propionicacid (A), i t s corresponding methyl ester methyl 3-(4.4-dimethyl-5-keto-isoxazo1e)propionate(2) and amide 3-(4.4-dimethyl-5-keto-