反应详情

温度

-78 °C

To a suspension of (2S)-2-(4-bromophenyl)-4-((1R)-1-phenylethyl)morpholine (3.46 g, 10.0 mmol) in tetrahydrofuran (80 ml) was added n-butyllithium (7.7 ml, 12.0 mmol, 1.56 M in hexane) at −78° C. After stirring the mixture for 10 minutes, excess of dry ice was added to the mixture and the reaction mixture was maintained at −78° C. for 1.5 hours and then partitioned between diethyl ether and 0.2 N aqueous sodium hydroxide. The aqueous layer was washed with diethyl ether and neutralized with 1N hydrochloric acid. The resulting aqueous layer was extracted with ethyl acetate. The organic layer was washed with brine, dried over sodium sulfate and concentrated in vacuo. Filtration of the precipitate gave 4-[(2S)-4-((1R)-1-phenyl-ethy)-morpholin-2-yl]-benzoic acid (3.05 g, 98%) as white crystals.

1. custompartitioned between diethyl ether and 0.2 N aqueous sodium hydroxide
2. washThe aqueous layer was washed with diethyl ether and neutralized with 1N hydrochloric acid
3. extractionThe resulting aqueous layer was extracted with ethyl acetate
4. washThe organic layer was washed with brine
5. dry with materialdried over sodium sulfate
6. concentrationconcentrated in vacuo
7. filtrationFiltration of the precipitate