O-(4-溴苯基)羟胺;盐酸盐

反应条件: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

实验步骤: The product of Example 29, step A (1.0 g, 4.45 mmol) and cyclohexane-1,3-dione (750 mg, 6.68 mmol) were reacted following the procedure of Example 44, step A. Purification by flash column chromatography (SiO2, 90:10 hexanes/ethyl acetate) provided 8-bromo-3,4-dihydrodibenzo[b,d]furan-1(2H)-one (410 mg, 35%) as a pale yellow solid: 1H NMR (CDCl3, 300 MHz) δ 8.20 (d, J=1.8 Hz, 1H), 7.42 (dd, J=8.7, 2.1 Hz, 1H), 7.33 (dd, J=8.7, 2.7 Hz, 1H), 3.04 (t, J=6.3 Hz, 2H), 2.61 (t, J=6.0 Hz, 2H), 2.28 (m, 2H). Purification by flash column chromatography (SiO2, 90:10 hexanes/ethyl acetate)

反应条件: temp:0.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

实验步骤: The product of step A (13.7 g, 61.02 mmol) and tert-butyl 4-oxopiperidine-1-carboxylate (13.37 g, 67.12 mmol) in acetic acid (36 mL) and concentrated sulfuric acid (4 mL) were heated to 110° C. for 2 h. After concentrating in vacuo the reaction mixture was diluted with dichloromethane (100 mL) and water (200 mL), basified with saturated aqueous potassium carbonate solution at 0° C. and extracted with dichloromethane. The organic extracts were dried over sodium sulfate, filtered and concentrated in vacuo. The residue was dissolved in 2-propanol (102 mL) and water (120 mL) before addition of potassium carbonate (9.5 g, 68.95 mmol) and di-tert-butyl dicarbonate (15 g, 68.9 mmol). The reaction mixture was stirred at 0° C. for 2 h then diluted with water (200 mL) and extracted three times with dichloromethane. The organic extracts were dried over sodium sulfate, filtered and concentrated in vacuo. The residue was purified by flash column chromatography (SiO2, 90:10 hexane/ethyl acetate) to give tert-butyl 8-bromo-3,4-dihydrobenzofuro[3,2-c]pyridine-2(1H)-carboxylate (8.7 g, 40%) as a light-pink solid: 1H NMR (CDCl3, 300 MHz) δ 7.53 (d, J=1.2 Hz, 1H), 7.36-7.25 (m, 2H), 4.51 (s, 2H), 3.82 (t, J=5.4 Hz, 2H), 2.84 (t, J=5.4 Hz, 2H), 1.50 (s, 9H). After concentrating in vacuo the reaction mixture was diluted with dichloromethane (100 mL) and water (200 mL) basified with saturated aqueous potassium carbonate solution at 0° C. extracted with dichloromethane The organic extracts were dried over sodium sulfate filtered concentrated in vacuo The residue was dissolved in 2-propanol (102 mL) extracted three times with dichloromethane The organic extracts were dried over sodium sulfate filtered concentrated in vacuo The residue was purified by flash column chromatography (SiO2, 90:10 hexane/ethyl acetate)