反应详情

温度

20 °C

Combine 5-[2-(tert-butyl(dimethyl)silyl)oxyethyl]-7H-pyrido[2,3-d][3]benzazepin-6-one (30.0 g, 0.08 mol) and toluene (300.0 mL), cool the reaction mixture to −10-0° C. Add potassium tert-butoxide (18.2 g, 0.16 mol), isoamyl nitrite (13.34 g, 0.11 mol) and then stir for 3-5 hours. Transfer the reaction mixture to a cool (0-5° C.) biphasic solution of ethyl acetate (210 mL) and water (510 mL) and stir for 15-30 minutes. Warm the reaction mixture to 15-25° C. and separate the layers. Extract the aqueous layer with additional ethyl acetate (120 mL) and methyl tert-butyl ether (120 mL) and combine the organic layers. Concentrate the organic under reduced pressure to a solution volume of approximately 60-90 mL and then add toluene (240 mL) and ethyl acetate (75 mL). Filter the solution through silica gel (45.0 g), rinse the silica gel with a mixture of toluene (210 mL) and ethyl acetate (60 mL), and concentrate the filtrate under reduced pressure to a volume of approximately 75 mL. Add heptane (120 mL) and concentrate the mixture to a volume of approximately 60 mL and filter the resulting solids. Wash the filter cake with heptane (25 mL) and dry under vacuum to provide the title compound (28.3 g, 72.5%) as a yellow solid.

1. customseparate the layers
2. extractionExtract the aqueous layer with additional ethyl acetate (120 mL) and methyl tert-butyl ether (120 mL)
3. concentrationConcentrate the organic under reduced pressure to a solution volume of approximately 60-90 mL
4. filtrationFilter the solution through silica gel (45.0 g)
5. washrinse the silica gel
6. additionwith a mixture of toluene (210 mL) and ethyl acetate (60 mL)
7. concentrationconcentrate the filtrate under reduced pressure to a volume of approximately 75 mL
8. concentrationAdd heptane (120 mL) and concentrate the mixture to a volume of approximately 60 mL
9. filtrationfilter the resulting solids
10. washWash the filter cake with heptane (25 mL)
11. customdry under vacuum