反应详情

Sodium hydride (0.82 g, 23.0 mmol, 60% mineral oil dispersion) is added to a solution of 4-benzyloxycarbonylpiperazin-2-one (5.13 g, 21.9 mmol) in THF/DMF (75 mL, 3/1 v/v) at 0° C. The mixture is stirred for 5 minutes, then propargyl bromide (3.7 mL, 41.5 mmol) is added dropwise. The resulting solution is stirred for 1 hour then brought to room temperature and stirred for 2 hours. The reaction is quenched with saturated ammonium chloride solution then diluted with ethyl acetate and washed with water (4×) and brine. The organic layer is dried over MgSO4, filtered and concentrated to dryness. The residue is purified by column chromatography eluting with 5% MeOH/CH2Cl2 to give the product (5.96 g, 21.9 mmol) as a white solid. 1H NMR (CDCl3, 300 MHz) δ7.3 (m, 5H), 5.12 (s, 2H), 4.25 (s,2H), 4.16 (s, 2H), 3.75 (m, 2H), 3.47 (m, 2H), 2.22 (s, 1H).

1. stirringThe resulting solution is stirred for 1 hour
2. customthen brought to room temperature
3. stirringstirred for 2 hours
4. customThe reaction is quenched with saturated ammonium chloride solution
5. additionthen diluted with ethyl acetate
6. washwashed with water (4×) and brine
7. dry with materialThe organic layer is dried over MgSO4
8. filtrationfiltered
9. concentrationconcentrated to dryness
10. customThe residue is purified by column chromatography
11. washeluting with 5% MeOH/CH2Cl2