反应详情

温度

-78 °C

The above N-(1-benzyl-4-piperidylidene)cyclohexylamine (4.81 g (17.69 mmol)) was dissolved in 150 ml of tetrahydrofuran. After this solution was cooled to -78° C., 13.3 ml (21.2 mmol) of 1.6 M n-butyl lithium in hexane was added dropwise. After the reaction mixture was stirred for 30 minutes under ice-cooling, a solution of 4.01 g (23.0 mmol) of tert-butyldimethylsiloxyacetaldehyde in 50 ml of tetrahydrofuran was added, followed by stirring for 1 hour under ice-cooling. To the reaction mixture, aqueous ammonium chloride was added, followed by stirring for 10 minutes and 3 extractions with ethyl acetate. The combined organic layer was dried over anhydrous magnesium sulfate; the solvent was distilled off under reduced pressure. The resulting residue was purified by silica gel column chromatography (hexane/ethyl acetate=3/1) to yield 1-benzyl-3-(2-tert-butyldimethylsiloxy-1-hydroxyethyl)-4-piperidinone.

1. temperaturecooling
2. stirringby stirring for 1 hour under ice-
3. temperaturecooling
4. stirringby stirring for 10 minutes
5. extraction3 extractions with ethyl acetate
6. dry with materialThe combined organic layer was dried over anhydrous magnesium sulfate
7. distillationthe solvent was distilled off under reduced pressure
8. customThe resulting residue was purified by silica gel column chromatography (hexane/ethyl acetate=3/1)