反应详情

Sixty-percent sodium hydride (480 mg, 12 mmols) was washed with petroleum ether, and then suspended in 40 ml of dimethyl sulfoxide. To the suspension were added 2.0 g (10 mmols) of 5,11-dihydrodibenzo[b,e][1,4]oxazepine. The mixture was stirred in a nitrogen atmosphere at room temperature for 30 minutes. To this reaction solution was added dropwise a solution of 8.8 g (35 mmols) of (R)-(-)-3-chloro-1-(4-methoxyphenethyl)piperidine [[α]D25 =-7.4 (c=1.1, ethanol)] in 30 ml of dimethyl sulfoxide at room temperature, and the mixed solution was stirred for 90 hours. The reaction solution was poured into ice water, and extracted with ethyl acetate. The organic layer was washed with water and with a saturated aqueous solution of sodium chloride in this order, and dried. Subsequently, the solvent was distilled off under reduced pressure. The resulting residue was subjected to column chromatography, and eluted with a mixed solvent of ethyl acetate and hexane at a ratio of 1:2. This mixed solvent was distilled off under reduced pressure to give 12.0 g of (S)-(-)-5,11-dihydro-5-[1-(4-methoxyphenethyl)-2-pyrrolidinylmethyl]dibenzo[b,e][1,4]oxazepine as a pale yellow oil in a yield of 80%.

1. stirringthe mixed solution was stirred for 90 hours
2. extractionextracted with ethyl acetate
3. washThe organic layer was washed with water and with a saturated aqueous solution of sodium chloride in this order
4. customdried
5. distillationSubsequently, the solvent was distilled off under reduced pressure
6. washeluted with a mixed solvent of ethyl acetate and hexane at a ratio of 1:2
7. distillationThis mixed solvent was distilled off under reduced pressure