反应详情

1.5 g (37.5 mmol) of 60% sodium hydride in oil was suspended in 50 mL of DMF to which was added 5.0 g (18.7 mmol) of 1-Boc-2-Cbz-hydrazine dissolved in 20 mL of dry DMF slowly over 30 minutes. The reaction mixture was stirred for 1 hour until H2 evolution had ceased. To this mixture was added 2.24 mL (18.77 mmol) of 1,4-dibromobutane neat. The reaction mixture was stirred at room temperature over 3 days. The mixture was concentrated in vacuo and the residue was suspended in 150 mL of EtOAc. The mixture was washed with water twice, 5% citric acid twice, saturated aqueous NaHCO3 solution , water and brine. The solution was dried over MgSO4, filtered and concentrated in vacuo. The residue was purified by flash chromatography over silica gel eluting with 30% EtOAc/hexanes to give the desired product as a white solid. 1H-NMR (CDCl3, 400 MHz):1.45 (bs, 9H); 1.62 (bm, 4H); 2.90 (bs, 2H); 4.15 (bm, 2H); 5.00-5.30 (m, 2H); 7.20-7.40 (bm, 5H).

1. stirringThe reaction mixture was stirred at room temperature over 3 days
2. concentrationThe mixture was concentrated in vacuo
3. washThe mixture was washed with water twice
4. dry with materialThe solution was dried over MgSO4
5. filtrationfiltered
6. concentrationconcentrated in vacuo
7. customThe residue was purified by flash chromatography over silica gel eluting with 30% EtOAc/hexanes