Reaktion #1012629

Reaktionsgleichung

[5-(5-bromo-2-fluoro-phenyl)-5-methyl-5,6-dihydro-2H-[1,4]oxazin-3-yl]-carbamic acid tert-butyl ester

water

sodium ascorbate

sodium azide

→

[5-(5-Azido-2-fluoro-phenyl)-5-methyl-5,6-dihydro-2H-[1,4]oxazin-3-yl]-carbamic acid tert-butyl ester

Lösungsmittel

EtOH

Reaktionsbedingungen

Aufarbeitung

1. 1
   SonstigeThe reaction mixture was degassed with Ar
2. 2
   Temperaturcooled to rt
3. 3
   Filtrationfiltered through silica gel
4. 4
   Einengenconcentrated
5. 5
   SonstigeThe resulting title compound was purified by FC (cyclohexane:EtOAc 100.0 to 80:20)

Vorschrift

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).

Quelle