tert-Butanol → HCID 68558515, compound

Participants

Reaction Conditions

Reaction Steps

[3-(3,4-Dichloro-phenyl)-4,5-dihydro-isoxazol-4-yl]-acetic acid (1 eq) was added to warm tert-butanol (10 vol) at 30° C. Triethylamine (1 eq) was then added and the mixture stirred for 5 minutes. DPPA (1 eq) was then added and the mixture was heated to 80° C. for 1 day. The tert-butanol was concentrated, water (20 vol) was added and the organics extracted with EtOAc (15 vol). The organic phase was washed with a mixture of acidified (2N citric acid) water & brine (>10 vol), a mixture of saturated NaHCO3 and brine (10 vol), dried over MgSO4, filtered and concentrated. The crude residue was purified by flash column chromatography (eluent: EtOAc:heptane) to yield [3-(3,4-Dichloro-phenyl)-4,5-dihydro-isoxazol-4-ylmethyl]-carbamic acid tert-butyl ester.

Provenance & Evidence