tert-butyl N-[2-(4-fluorophenoxy)ethyl]carbamate

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

实验步骤: Next, to a solution of [2-(4-fluorophenoxy)ethyl]carbamic acid tert-butyl ester (7.0 g, 27.4 mmol) in dioxane (20 mL) cooled in an ice bath was added 4N—HCl in dioxane (100 mL) dropwise. The mixture was stirred at 0° C. for 2 hours, and at room temperature for 16 hours. The precipitates were filtered, washed with diethylether, and dried under reduced pressure to yield 2-(4-fluorophenoxy)ethylamine HCl salt (4.24 g, 80.7% yield). at room temperature for 16 hours The precipitates were filtered washed with diethylether dried under reduced pressure

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

实验步骤: Next, to a solution of 4-fluorophenol (0.47 g, 4.18 mmol) in DMF (10 mL) was added cesium carbonate (2.72 g, 8.36 mmol) at room temperature. The mixture was stirred at ambient temperature for 15 minutes, then methanesulfonic acid 2-(tert-butoxycarbonylamino)ethyl ester (1.00 g, 4.18 mmol) was added. The reaction mixture was stirred at 100° C. for 16 hours. Water was added and the mixture was concentrated in vacuo. Product mixture was dissolved in ethyl acetate and was washed with water, then with brine. The organic layer was dried over Na2SO4, and the solvent was removed under reduced pressure. The residue was purified by column chromatography (ethyl acetate:hexane=7:1 to 4:1), and obtained [2-(4-fluorophenoxy)ethyl]carbamic acid tert-butyl ester as yellow oil (0.61 g, 57.4% yield). The reaction mixture was stirred at 100° C. for 16 hours the mixture was concentrated in vacuo Product mixture was dissolved in ethyl acetate was washed with water The organic layer was dried over Na2SO4 the solvent was removed under reduced pressure The residue was purified by column chromatography (ethyl acetate:hexane=7:1 to 4:1)

反应条件: temp:0.00; pressure:0.00; stir:

反应条件: temp:0.00; pressure:0.00; stir:

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

实验步骤: Next, to a solution of [2-(4-fluorophenoxy)ethyl]carbamic acid tert-butyl ester (7.0 g, 27.4 mmol) in dioxane (20 mL) cooled in an ice bath was added 4N—HCl in dioxane (100 mL) dropwise. The mixture was stirred at 0° C. for 2 hours, and at room temperature for 16 hours. The precipitates were filtered, washed with diethylether, and dried under reduced pressure to yield 2-(4-fluorophenoxy)ethylamine HCl salt (4.24 g, 80.7% yield). at room temperature for 16 hours The precipitates were filtered washed with diethylether dried under reduced pressure

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

实验步骤: Next, to a solution of 4-fluorophenol (0.47 g, 4.18 mmol) in DMF (10 mL) was added cesium carbonate (2.72 g, 8.36 mmol) at room temperature. The mixture was stirred at ambient temperature for 15 minutes, then methanesulfonic acid 2-(tert-butoxycarbonylamino)ethyl ester (1.00 g, 4.18 mmol) was added. The reaction mixture was stirred at 100° C. for 16 hours. Water was added and the mixture was concentrated in vacuo. Product mixture was dissolved in ethyl acetate and was washed with water, then with brine. The organic layer was dried over Na2SO4, and the solvent was removed under reduced pressure. The residue was purified by column chromatography (ethyl acetate:hexane=7:1 to 4:1), and obtained [2-(4-fluorophenoxy)ethyl]carbamic acid tert-butyl ester as yellow oil (0.61 g, 57.4% yield). The reaction mixture was stirred at 100° C. for 16 hours the mixture was concentrated in vacuo Product mixture was dissolved in ethyl acetate was washed with water The organic layer was dried over Na2SO4 the solvent was removed under reduced pressure The residue was purified by column chromatography (ethyl acetate:hexane=7:1 to 4:1)

反应条件: temp:90.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

实验步骤: To the crude product (700 mg) of t-butyl 2-bromoethylcarbamate obtained in Step 1 were added 4-fluorophenol (875 mg), potassium carbonate (1.08 g) and DMF (7 ml), and the mixture was stirred overnight at 90° C. The solvent was evaporated, and the mixture was diluted with ethyl acetate. After washing with water, the organic layer was dried over anhydrous sodium sulfate, and the solvent was evaporated. The obtained crude product was purified by silica gel chromatography (ethyl acetate-hexane) to give t-butyl 2-(4-fluorophenoxy)ethylcarbamate (390 mg). The solvent was evaporated the mixture was diluted with ethyl acetate After washing with water the organic layer was dried over anhydrous sodium sulfate the solvent was evaporated The obtained crude product was purified by silica gel chromatography (ethyl acetate-hexane)

反应条件: temp:0.00; pressure:0.00; stir:

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

实验步骤: Next, to a solution of [2-(4-fluorophenoxy)ethyl]carbamic acid tert-butyl ester (7.0 g, 27.4 mmol) in dioxane (20 mL) cooled in an ice bath was added 4N—HCl in dioxane (100 mL) dropwise. The mixture was stirred at 0° C. for 2 hours, and at room temperature for 16 hours. The precipitates were filtered, washed with diethylether, and dried under reduced pressure to yield 2-(4-fluorophenoxy)ethylamine HCl salt (4.24 g, 80.7% yield). at room temperature for 16 hours The precipitates were filtered washed with diethylether dried under reduced pressure

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

实验步骤: Next, to a solution of 4-fluorophenol (0.47 g, 4.18 mmol) in DMF (10 mL) was added cesium carbonate (2.72 g, 8.36 mmol) at room temperature. The mixture was stirred at ambient temperature for 15 minutes, then methanesulfonic acid 2-(tert-butoxycarbonylamino)ethyl ester (1.00 g, 4.18 mmol) was added. The reaction mixture was stirred at 100° C. for 16 hours. Water was added and the mixture was concentrated in vacuo. Product mixture was dissolved in ethyl acetate and was washed with water, then with brine. The organic layer was dried over Na2SO4, and the solvent was removed under reduced pressure. The residue was purified by column chromatography (ethyl acetate:hexane=7:1 to 4:1), and obtained [2-(4-fluorophenoxy)ethyl]carbamic acid tert-butyl ester as yellow oil (0.61 g, 57.4% yield). The reaction mixture was stirred at 100° C. for 16 hours the mixture was concentrated in vacuo Product mixture was dissolved in ethyl acetate was washed with water The organic layer was dried over Na2SO4 the solvent was removed under reduced pressure The residue was purified by column chromatography (ethyl acetate:hexane=7:1 to 4:1)

反应条件: temp:90.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

实验步骤: To the crude product (700 mg) of t-butyl 2-bromoethylcarbamate obtained in Step 1 were added 4-fluorophenol (875 mg), potassium carbonate (1.08 g) and DMF (7 ml), and the mixture was stirred overnight at 90° C. The solvent was evaporated, and the mixture was diluted with ethyl acetate. After washing with water, the organic layer was dried over anhydrous sodium sulfate, and the solvent was evaporated. The obtained crude product was purified by silica gel chromatography (ethyl acetate-hexane) to give t-butyl 2-(4-fluorophenoxy)ethylcarbamate (390 mg). The solvent was evaporated the mixture was diluted with ethyl acetate After washing with water the organic layer was dried over anhydrous sodium sulfate the solvent was evaporated The obtained crude product was purified by silica gel chromatography (ethyl acetate-hexane)

反应条件: temp:90.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

实验步骤: To the crude product (700 mg) of t-butyl 2-bromoethylcarbamate obtained in Step 1 were added 4-fluorophenol (875 mg), potassium carbonate (1.08 g) and DMF (7 ml), and the mixture was stirred overnight at 90° C. The solvent was evaporated, and the mixture was diluted with ethyl acetate. After washing with water, the organic layer was dried over anhydrous sodium sulfate, and the solvent was evaporated. The obtained crude product was purified by silica gel chromatography (ethyl acetate-hexane) to give t-butyl 2-(4-fluorophenoxy)ethylcarbamate (390 mg). The solvent was evaporated the mixture was diluted with ethyl acetate After washing with water the organic layer was dried over anhydrous sodium sulfate the solvent was evaporated The obtained crude product was purified by silica gel chromatography (ethyl acetate-hexane)