反应详情

温度

60 °C

To (R)-(−)-1-phenyl-1,2,9,10-tetrahydro[1,4]oxazino[2,3,4-jk]carbazol-7(8H)-one (17.3 g, 57.3 mmol) in dry DMF (60 mL) is added anhydrous cupric chloride (17.7 g, 131.8 mmol) and anhydrous lithium chloride (9.6 g, 229 mmol). The mixture is heated at 60° C. for 40 h. The mixture is then poured into water (600 mL), forming solids. The solids are dissolved in ethyl acetate (50 mL) and filtered to remove inorganic solids. The filtrates are concentrated to dryness and the resulting solids are dissolved in DMF (60 mL), to which is added lithium bromide (12.4 g, 143 mmol) and lithium carbonate (10.6 g, 143 mmol). The mixture is heated at 120° C. for 6 h, cooled, then partitioned between water and CH2Cl2, and the organic layer washed three times with water (200 mL). Column chromatography (600 mL silica) is performed using EtOAc/hexanes (20/80) as eluent. The material is then rechromatographed (600 mL silica) using EtOAc/hexane (20/80) as eluent to give 6.0 g (35%) of (R)-(−)-1-phenyl-1,2-dihydro[1,4]oxazino[2,3,4-jk]carbazol-7-ol; [□]25D=−121° (c 0.73, methylene chloride).

1. customforming solids
2. filtrationfiltered
3. customto remove inorganic solids
4. concentrationThe filtrates are concentrated to dryness
5. dissolutionthe resulting solids are dissolved in DMF (60 mL), to which
6. temperatureThe mixture is heated at 120° C. for 6 h
7. temperaturecooled
8. custompartitioned between water and CH2Cl2
9. washthe organic layer washed three times with water (200 mL)
10. customThe material is then rechromatographed (600 mL silica)