反应详情

To a solution of 2-Amino-indan-2-carboxylic acid (0.45 g, 1.63 mmol) in CH2Cl2 (16 mL) was added HCl (in dioxanes, 4 M, 0.41 mL, 1.63 mmol). The solution was stirred at room temperature for 2 h and concentrated to dryness. The crude oil was dissolved in THF (6.5 mL). Aqueous NaOH (6 M, 0.92 mL, 5.5 mmol) and Methyl Chloroformate (0.15 mL, 1.95 mmol) were added and the resulting slurry was stirred at room temperature for 18 h. The reaction was diluted with HCl (1N) and extracted with Et2O (3 times). The combined organic layers were extracted with NaOH (2N, 3 times). The aqueous layers were acidified with HCl (6 N) and extracted with Et2O (3 times). The combined organic layers were dried over MgSO4 and concentrated. The crude oil was diluted in hexanes and concentrated again to provide 2-Methoxycarbonylamino-indan-2-carboxylic acid (0.35 g, 92%). LCMS-ESI+: calc'd for C12H13NO4: 235.08 (M+); Found: 235.94 (M+H+).

1. concentrationconcentrated to dryness
2. dissolutionThe crude oil was dissolved in THF (6.5 mL)
3. stirringthe resulting slurry was stirred at room temperature for 18 h
4. extractionextracted with Et2O (3 times)
5. extractionThe combined organic layers were extracted with NaOH (2N, 3 times)
6. extractionextracted with Et2O (3 times)
7. dry with materialThe combined organic layers were dried over MgSO4
8. concentrationconcentrated
9. additionThe crude oil was diluted in hexanes
10. concentrationconcentrated again