反应详情

温度

120 °C

A mixture of 4-bromohexahydro-5-oxo-1H-azepine-1-carboxylic acid 1,1-dimethylethyl ester and 3-bromohexahydro-4-oxo-1H-azepine-1-carboxylic acid 1,1-dimethylethyl ester (0.22 g, 0.50 mmol) and trans-cinnamamide (0.06 g, 0.38 mmol) was supported in silica gel (1 g) and mechanically stirred at 120° C. for 3 days. The product was eluted from the silica gel with a 7M solution of ammonia in MeOH and the filtrate evaporated in vacuo. The crude product was basified with a saturated solution of NaHCO3 and extracted with DCM. The organic layer was separated, dried (Na2SO4), filtered and the solvent evaporated in vacuo to yield 5,6,7,8-tetrahydro-2-[(E)-2-phenylethenyl]-4H-oxazolo[4,5-d]azepine (0.045 g, 15% yield, 32% pure) as a brown solid that was used in the next step without further purification. C15H16N2O LCMS: Rt 1.60, m/z 241 [M+H]+ (method 5). The compound 3-bromohexahydro-4-oxo-1H-azepine-1-carboxylic acid 1,1-dimethylethyl ester was not observed in the crude of the reaction.

1. washThe product was eluted from the silica gel with a 7M solution of ammonia in MeOH
2. customthe filtrate evaporated in vacuo
3. extractionextracted with DCM
4. customThe organic layer was separated
5. dry with materialdried (Na2SO4)
6. filtrationfiltered
7. customthe solvent evaporated in vacuo