反应详情

To a stirred solution of tert-butyl (S)-1-(4-bromophenyl)ethyl(4-hydroxy-4-phenylbutyl)carbamate (3.24 g, 7.1 mmol) in CH2Cl2 (20 mL) at rt was added 15% Dess-Martin periodinane solution in CH2Cl2 (23 mL, 10.8 mmol). The mixture was stirred overnight at rt. Satd aq NaHCO3 (50 mL) was added and the mixture was stirred for 10 min Solid Na2S2O3 (5 g) was added and stirring was continued for 1 h. The mixture was extracted with CH2Cl2 (2×100 mL) and the combined organic layer was washed with brine (35 mL) and dried over Na2SO4. Removal of the solvent left an amber oil (3.19 g) which was purified by chromatography on a 40-g silica cartridge eluted with a 0-100% EtOAc in hexanes gradient to afford (S)-tert-butyl 1-(4-bromophenyl)ethyl(4-oxo-4-phenylbutyl)carbamate (2.32 g, 72%) as a yellow oil. LC-MS Method 1 tR=2.40 min, m/z=470, 468, 348, 346.

1. additionwas added
2. stirringstirring
3. waitwas continued for 1 h
4. extractionThe mixture was extracted with CH2Cl2 (2×100 mL)
5. washthe combined organic layer was washed with brine (35 mL)
6. dry with materialdried over Na2SO4
7. customRemoval of the solvent
8. waitleft an amber oil (3.19 g) which
9. customwas purified by chromatography on a 40-g silica cartridge
10. washeluted with a 0-100% EtOAc in hexanes gradient