反应详情

A mixture of crude 7-amino-8-bromo-9a-ethyl-4-methyl-1,2,9,9a-tetrahydro-3H-fluoren-3-one (0.97 g, 3.02 mmol), CuCN (0.318 g, 3.55 mmol), and 1-methyl-2-pyrrolidinone (NMP, 6 mL) was placed under a N2 atmosphere, stirred, and heated in an oil bath at 160–170° C. for 5.5 hours. After cooling to room temperature, the mixture was added to EtOAc (200 mL) and water (200 mL) and filtered through a pad of solka-floc. The organic portion of the filtrate was washed with water (5×200 mL) and brine (100 mL), dried over MgSO4, filtered, and evaporated under vacuum to a red oil (0.8 g). The crude product was purified by chromatography on EM silica gel 60 (2.75×25 cm column), eluting with 5% EtOAc in CH2Cl2, to afford 7-amino-8-cyano-9a-ethyl-4-methyl-1,2,9,9a-tetrahydro-3H-fluoren-3-one (0.48 g) as a solid.

1. temperatureheated in an oil bath at 160–170° C. for 5.5 hours
2. filtrationfiltered through a pad of solka-floc
3. washThe organic portion of the filtrate was washed with water (5×200 mL) and brine (100 mL)
4. dry with materialdried over MgSO4
5. filtrationfiltered
6. customevaporated under vacuum to a red oil (0.8 g)
7. customThe crude product was purified by chromatography on EM silica gel 60 (2.75×25 cm column)
8. washeluting with 5% EtOAc in CH2Cl2