5-Isopentyl-3-methylisoxazole → 2-Amino-7-methyloct-2-en-4-one

Participants

Reaction Steps

3-Methyl-5-(3-methylbutyl)isoxazole (3.90 g, 25.5 mmol) [synthesis analogous to C. Kashima et al., Bull. Chem. Soc. Jpn. 46, 310-313 (1973)] is introduced into 80 ml of ethanol, platinum(IV) oxide catalyst (390 mg, 1.72 mmol) is added, and the mixture is then hydrogenated under atmospheric pressure hydrogen for 2 h (slightly exothermic reaction). The catalyst is filtered off, the filtrate is concentrated, and the residue is purified by chromatography on a Biotage 40M cartridge (mobile phase: isohexane/ethyl acetate 3:1). The product fractions are concentrated. The resulting residue is an oil, which crystallizes after a short time. Drying in vacuo results in 3.41 g (86% of theory) of the title compound.

Provenance & Evidence