反応 #168699

反応方程式

[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

溶媒

water

ethanol

反応条件

後処理

1. 1
   抽出The mixture was extracted with EtOAc
2. 2
   洗浄the organic phase was washed with brine
3. 3
   乾燥dried with Na2SO4
4. 4
   その他evaporated under reduced pressure
5. 5
   その他The residue was purified by chromatography on silica gel (cyclohexane/EtOAc=7:3)

実験手順

[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.

出典