反应详情

温度

0 °C

Add trifluoroacetic acid (49.8 mL, 670 mmol) to [4-(3-methoxy-phenyl)-4-oxo-butyl]-carbamic acid tert-butyl ester (22.21 g, 67 mmol) with ice/water cooling. After stirring at 0° C. for 3.5 h, adjust the reaction to pH 10 with 50% sodium hydroxide. Extract the reaction mixture with ether (5×100 mL), dry the combined organic layers over magnesium sulfate, filter, and concentrate under reduced pressure to obtain the crude product (15.43 g). Purify by flash chromatography [silica gel, 330 g, 0 to 30% gradient of (90:10:1 methylene chloride/methanol/concentrated ammonium hydroxide) in methylene chloride] to obtain the title compound (10.76 g, 88% for two steps). MS (APCI+): 176 [C11H13NO+H]+; 1H NMR (300 MHz, CDCl3): δ 7.46-7.45 (m, 1H), 7.37-7.27 (m, 2H), 6.99-6.95 (m, 1H), 4.09-4.03 (m, 2H), 3.84 (s, 3H), 2.96-2.89 (m, 2H), 2.08-1.97 (m, 2H).

1. extractionExtract the reaction mixture with ether (5×100 mL)
2. dry with materialdry the combined organic layers over magnesium sulfate
3. filtrationfilter
4. concentrationconcentrate under reduced pressure
5. customto obtain the crude product (15.43 g)
6. customPurify by flash chromatography [silica gel, 330 g, 0 to 30% gradient of (90:10:1 methylene chloride/methanol/concentrated ammonium hydroxide) in methylene chloride]