반응 #168699

반응 방정식

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

sodium azide

sodium ascorbate

(1R,2R)—N,N′-dimethyl-cyclohexane-1,2-diamine

→

title compound

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

용매

water

ethanol

반응 조건

후처리

1. 1
   추출The mixture was extracted with EtOAc
2. 2
   세척the organic phase was washed with brine
3. 3
   건조dried with Na2SO4
4. 4
   기타evaporated under reduced pressure
5. 5
   기타The residue was purified by chromatography on silica gel (cyclohexane/EtOAc=7:3)

실험 절차

[5-(3-Bromo-phenyl)-5-methyl-5,6-dihydro-2H-[1,4]oxazin-3-yl]-carbamic acid tert-butyl ester (5.03 g, 12.67 mmol), sodium azide (1.647 g, 25.3 mmol), sodium ascorbate (0.125 g, 0.63 mmol), copper iodide (0.241 g, 1.27 mmol) and (1R,2R)—N,N′-dimethyl-cyclohexane-1,2-diamine (0.270 g, 1.90 mmol) were dissolved in ethanol (17.7 ml) and water (7.6 ml). The mixture was stirred under N2 at 90° C. for 4 h and then poured into 1M aqueous KHCO3 solution. The mixture was extracted with EtOAc, and the organic phase was washed with brine, dried with Na2SO4 and evaporated under reduced pressure. The residue was purified by chromatography on silica gel (cyclohexane/EtOAc=7:3) to yield the title compound.

출처