Water → HCID 89500641, compound

Participants

Reaction Conditions

Reaction Steps

A mixture of [5-(5-bromo-2-fluoro-phenyl)-5-methyl-5,6-dihydro-2H-[1,4]oxazin-3-yl]-carbamic acid tert-butyl ester (5.0 g, 12.91 mmol) in EtOH (50 ml) was homogenized in an ultrasound bath for 10 min. To this suspension was added water (22 ml), cyclohexane dimethyldiamine (0.611 ml, 0.551 g, 3.87 mmol), sodium ascorbate (0.512 g, 2.58 mmol), sodium azide (3.36 g, 51.6 mmol) and CuI (0.492 g, 2.58 mmol). The reaction mixture was degassed with Ar and heated for 1 h at 70° C., then cooled to rt, filtered through silica gel and concentrated. The resulting title compound was purified by FC (cyclohexane:EtOAc 100.0 to 80:20).

Provenance & Evidence