Sodium hydride → HCID 86705909、化合物

関与物質

反応条件

反応手順

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)+.

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