反应详情

温度

70 °C

To an ice-cooled solution of 8-benzylamino-6,7,8,9-tetrahydro-5H-benzocyclohepten-2-ol (1.7 g) in toluene (56 ml) was added portionwise sodium hydride (60% dispersion in mineral oil; 0.31 g). After the addition was complete, the mixture was stirred at 70° C. for 1 hour. After cooling, a mixture of ethyl bromoacetate (0.81 ml) and tetra-n-butylammonium bromide (0.10 g) in toluene (14 ml) was added, and the mixture was stirred at 70° C. for 4 hours. After cooling, the reaction mixture was poured into saturated aqueous ammonium chloride, and extracted once with ethyl acetate. The extract was washed with water and brine, dried over anhydrous sodium sulfate, and concentrated in vacuo. The residue was purified by column chromatography on silica gel (gradient elution; chloroform-ethanol; 25:1 to 5:1) to give N-benzyl-3-ethoxycarbonylmethoxy-6,7,8,9-tetrahydro-5H-benzocyclohepten-6-amine (2.0 g) as an oil.

1. additionAfter the addition
2. temperatureAfter cooling
3. additionwas added
4. stirringthe mixture was stirred at 70° C. for 4 hours
5. temperatureAfter cooling
6. extractionextracted once with ethyl acetate
7. washThe extract was washed with water and brine
8. dry with materialdried over anhydrous sodium sulfate
9. concentrationconcentrated in vacuo
10. customThe residue was purified by column chromatography on silica gel (gradient elution; chloroform-ethanol; 25:1 to 5:1)