反应详情

A solution of imidazole (253 mg, 3.72 mmol) in DMF (2 mL) was added to a suspension of NaH (60% in mineral oil, 164 mg, 4.10 mmol) in DMF (8 mL), and the mixture was stirred at room temperature for 45 minutes. A solution of toluene-4-sulfonic acid 2-tert-butoxycarbonylamino-ethyl ester (1.29 g, 4.09 mmol) in DMF (6 mL) was added, and the mixture was stirred at room temperature for 16 h then concentrated in vacuo. The residue was partitioned between H2O (25 mL) and EtOAc (25 mL), and the aqueous phase was extracted with EtOAc (25 mL). The combined organic phases were dried (MgSO4) and concentrated in vacuo. Purification of the crude material by column chromatography on silica gel (200:5:1-100:5:1 CH2Cl2/MeOH/NH4OH) gave a colourless oil (224 mg, 29%). 1H NMR (CDCl3) δ 1.44 (s, 9H), 3.43 (m, 2H), 4.08 (m, 2H), 4.64 (br s, 1H), 6.92 (s, 1H), 7.09 (s, 1H), 7.46 (s, 1H).

1. stirringthe mixture was stirred at room temperature for 16 h
2. concentrationthen concentrated in vacuo
3. customThe residue was partitioned between H2O (25 mL) and EtOAc (25 mL)
4. extractionthe aqueous phase was extracted with EtOAc (25 mL)
5. dry with materialThe combined organic phases were dried (MgSO4)
6. concentrationconcentrated in vacuo
7. customPurification of the crude material by column chromatography on silica gel (200:5:1-100:5:1 CH2Cl2/MeOH/NH4OH)