Sodium hydride → (5RS)-3-(3-Fluoro-4-iodophenyl)-5-(N-(t-butoxycarbonyl)isoxazol-3-ylaminomethyl)-4,5-dihydro-isoxazole

Participants

Reaction Steps

A solution of (5RS)-3-(3-Fluoro-4-iodophenyl)-5-methanesulfonyloxymethyl-4,5-dihydroisoxazole (1.7 g, 4.26 mM) in dry N,N-dimethylformamide (40 ml) under nitrogen, was treated with sodium hydride (60% in oil, 0.205 g, 5.13 mM), and stirred for 5 minutes. N-Allyl-3-(t-Butoxycarbonylamino)isoxazole (0.86 g, 4.69 mM) was added, and the mixture heated at 60° for 18 hours. After cooling and dilution with water (200 ml), the mixture was extracted with ethyl acetate (3×100 ml), the extracts were washed with water (2×100 ml), brine (100 ml), dried (magnesium sulfate). The residue after evaporation was purified by chromatography on a 50 g silica Mega Bond Elut® column, eluting with a mixture of 25% ethyl acetate in isohexane. Relevant fractions were combined to give the desired product (1.61 g). MS (ESP): 488 (MH+) for C18H19FIN3O4

Provenance & Evidence