tert-Butyl 4-ethenylpiperidine-1-carboxylate → Tert-butyl 4-(3-(6-(4-methoxybenzylcarbamoyl)-2-methylpyrimidin-4-yl)-4,5-dihydroisoxazol-5-yl)piperidine-1-carboxylate

Participants

Reaction Steps

To a cold solution of (6-((hydroxyimino)methyl)-N-(4-methoxybenzyl)-2-methylpyrimidine-4-carboxamide (0.2 g, 0.66 mmol, Preparation #B.1.1) and tert-butyl 4-vinylpiperidine-1-carboxylate (0.168 g, 0.799 mmol, Preparation #E.1.2) in chloroform (20 mL) was added iodobenzene diacetate (0.343 g, 1.06 mmol) in one portion. The mixture was allowed to warm to RT and stirred for about another 1 h. The reaction mixture was quenched with water (20 mL) and the product was extracted with chloroform (2×20 mL). The organic layer was washed with water (2×15 mL), dried over sodium sulphate and evaporated to dryness. The residue obtained was purified by column chromatography using silica gel (60-120 mesh) eluting with 50% n-hexane and EtOAc. Relevant fractions containing the required compound were combined and evaporated to dryness under reduced pressure to afford tert-butyl 4-(3-(6-(4-methoxybenzylcarbamoyl)-2-methylpyrimidin-4-yl)-4,5-dihydroisoxazol-5-yl)piperidine-1-carboxylate 0.1 g (29%). MS m/z: 510 (M+H)+.

Provenance & Evidence