反应详情

温度

5 °C

To a solution of 2.00 g of 1-azabicyclo[3.3.1]nonan-4-one in 100 ml of dimethoxyethane, 3.65 g of p-toluenesulfonylmethylisocyanide and 1.13 g of ethanol were added, followed by cooling to 5° C. Then, 4.00 g of potassium tert-butoxide was added while keeping the internal temperature below 10° C. The mixture was stirred at room temperature for 30 minutes, followed by further stirring at 40° C. for 30 minutes. The precipitate thus formed was removed by filtration. The residue obtained by evaporation of the solvent was purified by an alumina column chromatography (eluent: chloroform:hexane=1:1). The resulting crude product was then purified by silica gel column chromatography (eluent: chloroform:methanol=20:1), whereby 1.01 g of (4R*,5R*)-1-azabicyclo[3.3.1]nonane-4-carbonitrile was obtained.

1. customthe internal temperature below 10° C
2. stirringby further stirring at 40° C. for 30 minutes
3. customThe precipitate thus formed
4. customwas removed by filtration
5. customThe residue obtained by evaporation of the solvent
6. customwas purified by an alumina column chromatography (eluent: chloroform:hexane=1:1)
7. customThe resulting crude product was then purified by silica gel column chromatography (eluent: chloroform:methanol=20:1)