反应详情

温度

0 °C

To a 0° C. solution of (S)-tert-butyl (1-hydroxy-3-phenylpropan-2-yl)carbamate (Alfa Aesar, 500 mg, 1.99 mmol) in DMF (13.0 mL) was added NaH (60% in mineral oil, 119 mg, 2.98 mmol). The resulting reaction mixture was stirred at 0° C. for 15 min and then (2-bromoethoxy)(tert-butyl)dimethylsilane (512 μL, 2.39 mmol) was added. The reaction mixture was stirred at 0° C. for 2 h and then at room temperature for 3 h. The mixture was poured into a separatory funnel containing EtOAc and sat. aq. NH4Cl. The aqueous layer was extracted with EtOAc (3×), and the combined organics were washed with sat. NaCl, dried over Na2SO4, filtered and concentrated in vacuo. The crude oil was purified using flash chromatography (40 g column, gradient from 0% to 40% EtOAc/hexanes over 14 min) to give the title compound (124 mg, 15%) as a colorless oil. MS (ESI+) m/z 310.1 (M+H−Boc)+.

1. customThe resulting reaction mixture
2. stirringThe reaction mixture was stirred at 0° C. for 2 h
3. waitat room temperature for 3 h
4. additionThe mixture was poured into a separatory funnel
5. extractionThe aqueous layer was extracted with EtOAc (3×)
6. washthe combined organics were washed with sat. NaCl
7. dry with materialdried over Na2SO4
8. filtrationfiltered
9. concentrationconcentrated in vacuo
10. customThe crude oil was purified
11. customflash chromatography (40 g column, gradient from 0% to 40% EtOAc/hexanes over 14 min)