benzyl N-(4-bromophenyl)carbamate

Conditions: temp:0.00; pressure:0.00; stir:

Conditions: temp:-78.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: To a solution of N-(carbobenzyloxy)-4-bromoaniline (5.00 g) in dry tetrahydrofuran (80 mL) at -78° C. under N2 is added n-butyllithium (21.4 mL, 1.6M in hexanes) dropwise over five minutes. The resulting yellow solution is stirred at -78° C. for 30 minutes and is then treated with a solution of N-(carbobenzyloxy)-4-piperidone (3.99 g) in dry tetrahydrofuran (17 mL). The reaction mixture is stirred for three hours, during which the reaction temperature is allowed to rise to 0° C., and is quenched with saturated aqueous ammonium chloride (30 mL). The mixture is then diluted with water (100 mL), the layers are separated, the aqueous phase is extracted with diethyl ether, and the combined organic phase is washed with saline (50 mL), dried over anhydrous sodium sulfate, and concentrated under reduced pressure. The residue is chromato-graphed on silica gel (230-400 mesh, 350 g), eluting with ethyl acetate/hexane (25/75), and those fractions with an Rf =0.38 by TLC (ethyl acetate/hexane, 50/50) are pooled and con-centrated under reduced pressure to give the title compound, mp 156° C.-158° C. The reaction mixture is stirred for three hours, during which the reaction temperature to rise to 0° C. is quenched with saturated aqueous ammonium chloride (30 mL) The mixture is then diluted with water (100 mL) the layers are separated the aqueous phase is extracted with diethyl ether the combined organic phase is washed with saline (50 mL) dried over anhydrous sodium sulfate concentrated under reduced pressure eluting with ethyl acetate/hexane (25/75)

Conditions: temp:-78.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: To a solution of N-(carbobenzyloxy)-4-bromoaniline (5.00 g) in dry tetrahydrofuran (80 mL) at -78° C. under N2 is added n-butyllithium (21.4 mL, 1.6M in hexanes) dropwise over five minutes. The resulting yellow solution is stirred at -78° C. for 30 minutes and is then treated with a solution of N-(carbobenzyloxy)-4-piperidone (3.99 g) in dry tetrahydrofuran (17 mL). The reaction mixture is stirred for three hours, during which the reaction temperature is allowed to rise to 0° C., and is quenched with saturated aqueous ammonium chloride (30 mL). The mixture is then diluted with water (100 mL), the layers are separated, the aqueous phase is extracted with diethyl ether, and the combined organic phase is washed with saline (50 mL), dried over anhydrous sodium sulfate, and concentrated under reduced pressure. The residue is chromato-graphed on silica gel (230-400 mesh, 350 g), eluting with ethyl acetate/hexane (25/75), and those fractions with an Rf =0.38 by TLC (ethyl acetate/hexane, 50/50) are pooled and con-centrated under reduced pressure to give the title compound, mp 156° C.-158° C. The reaction mixture is stirred for three hours, during which the reaction temperature to rise to 0° C. is quenched with saturated aqueous ammonium chloride (30 mL) The mixture is then diluted with water (100 mL) the layers are separated the aqueous phase is extracted with diethyl ether the combined organic phase is washed with saline (50 mL) dried over anhydrous sodium sulfate concentrated under reduced pressure eluting with ethyl acetate/hexane (25/75)

Conditions: temp:-78.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: To a solution of N-(carbobenzyloxy)-4-bromoaniline (5.00 g) in dry tetrahydrofuran (80 mL) at −78° C. under N2 is added n-butyllithium (21.4 mL, 1.6 M in hexanes) dropwise over five minutes. The resulting yellow solution is stirred at −78° C. for 30 minutes and is then treated with a solution of N-(carbobenzyloxy)-4-piperidone (3.99 g) in dry tetrahydrofuran (17 mL). The reaction mixture is stirred for three hours, during which the reaction temperature is allowed to rise to 0° C., and is quenched with saturated aqueous ammonium chloride (30 mL). The mixture is then diluted with water (100 mL), the layers are separated, the aqueous phase is extracted with diethyl ether, and the combined organic phase is washed with saline (50 mL), dried over anhydrous sodium sulfate, and concentrated under reduced pressure. The residue is chromato-graphed on silica gel (230-400 mesh, 350 g), eluting with ethyl acetate/hexane (25/75), and those fractions with an Rf=0.38 by TLC (ethyl acetate/hexane, 50/50) are pooled and con-centrated under reduced pressure by give the title compound, mp 156° C.-158° C. The reaction mixture is stirred for three hours, during which the reaction temperature to rise to 0° C. is quenched with saturated aqueous ammonium chloride (30 mL) The mixture is then diluted with water (100 mL) the layers are separated the aqueous phase is extracted with diethyl ether the combined organic phase is washed with saline (50 mL) dried over anhydrous sodium sulfate concentrated under reduced pressure eluting with ethyl acetate/hexane (25/75)

Conditions: temp:-78.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: To a solution of N-(carbobenzyloxy)-4-bromoaniline (5.00 g) in dry tetrahydrofuran (80 mL) at −78° C. under N2 is added n-butyllithium (21.4 mL, 1.6 M in hexanes) dropwise over five minutes. The resulting yellow solution is stirred at −78° C. for 30 minutes and is then treated with a solution of N-(carbobenzyloxy)-4-piperidone (3.99 g) in dry tetrahydrofuran (17 mL). The reaction mixture is stirred for three hours, during which the reaction temperature is allowed to rise to 0° C., and is quenched with saturated aqueous ammonium chloride (30 mL). The mixture is then diluted with water (100 mL), the layers are separated, the aqueous phase is extracted with diethyl ether, and the combined organic phase is washed with saline (50 mL), dried over anhydrous sodium sulfate, and concentrated under reduced pressure. The residue is chromato-graphed on silica gel (230-400 mesh, 350 g), eluting with ethyl acetate/hexane (25/75), and those fractions with an Rf=0.38 by TLC (ethyl acetate/hexane, 50/50) are pooled and con-centrated under reduced pressure by give the title compound, mp 156° C.-158° C. The reaction mixture is stirred for three hours, during which the reaction temperature to rise to 0° C. is quenched with saturated aqueous ammonium chloride (30 mL) The mixture is then diluted with water (100 mL) the layers are separated the aqueous phase is extracted with diethyl ether the combined organic phase is washed with saline (50 mL) dried over anhydrous sodium sulfate concentrated under reduced pressure eluting with ethyl acetate/hexane (25/75)

Conditions: temp:0.00; pressure:0.00; stir:

Conditions: temp:-78.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: To a solution of N-(carbobenzyloxy)-4-bromaniline (5.00 g) in dry tetrahydrofuran (80 mL) at -78° C. under N2 is added n-butyllithium (21.4 mL, 1.6 M in hexanes) dropwise over five minutes. The resulting yellow solution is stirred at -78° C. for 30 minutes and is then treated with a solution of N-(carbobenzyloxy)-4-piperidone (3.99 g) in dry tetrahydrofuran (17 mL). The reaction mixture is stirred for three hours, during which the reaction temperature is allowed to rise to 0° C. and is quenched with saturated aqueous ammonium chloride (30 mL). The mixture is then diluted with water (100 mL), the layers are separated, the aqueous phase is extracted with diethyl ether, and the combined organic phase is washed with saline (50 mL), dried over anhydrous sodium sulfate, and concentrated under reduced pressure. The residue is chromato-graphed on silica gel (230-400 mesh, 350 g), eluting with ethyl acetate/hexane (25/75), and those fractions with an Rf =0.38 by TLC (ethyl acetate/hexane, 50/50) are pooled and concentrated under reduced pressure to give the title compound, mp 156° C.-158° C. The reaction mixture is stirred for three hours, during which the reaction temperature to rise to 0° C. is quenched with saturated aqueous ammonium chloride (30 mL) The mixture is then diluted with water (100 mL) the layers are separated the aqueous phase is extracted with diethyl ether the combined organic phase is washed with saline (50 mL) dried over anhydrous sodium sulfate concentrated under reduced pressure eluting with ethyl acetate/hexane (25/75) concentrated under reduced pressure

Conditions: temp:-78.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: To a solution of N-(carbobenzyloxy)-4-bromoaniline (5.00 g) in dry tetrahydrofuran (80 mL) at -78° C. under N2 is added n-butyllithium (21.4 mL, 1.6 M in hexanes) dropwise over five minutes. The resulting yellow solution is stirred at -78° C. for 30 minutes and is then treated with a solution of N-(carbobenzyloxy)-4-piperidone (3.99 g) in dry tetrahydrofuran (17 mL). The reaction mixture is stirred for three hours, during which the reaction temperature is allowed to rise to 0° C., and is quenched with saturated aqueous ammonium chloride (30 mL). The mixture is then diluted with water (100 mL), the layers are separated, the aqueous phase is extracted with diethyl ether, and the combined organic phase is washed with saline (50 mL), dried over anhydrous sodium sulfate, and concentrated under reduced pressure. The residue is chromato-graphed on silica gel (230-400 mesh, 350 g), eluting with ethyl acetate/hexane (25/75), and those fractions with an Rf =0.38 by TLC (ethyl acetate/hexane, 50/50) are pooled and con-centrated under reduced pressure to give the title compound, mp 156° C.-158° C. The reaction mixture is stirred for three hours, during which the reaction temperature to rise to 0° C. is quenched with saturated aqueous ammonium chloride (30 mL) The mixture is then diluted with water (100 mL) the layers are separated the aqueous phase is extracted with diethyl ether the combined organic phase is washed with saline (50 mL) dried over anhydrous sodium sulfate concentrated under reduced pressure eluting with ethyl acetate/hexane (25/75)

Conditions: temp:-78.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: To a solution of N-(carbobenzyloxy)-4-bromoaniline (5.00 g) in dry tetrahydrofuran (80 mL) at -78° C. under N2 is added n-butyllithium (21.4 mL, 1.6M in hexanes) dropwise over five minutes. The resulting yellow solution is stirred at -78° C. for 30 minutes and is then treated with a solution of N-(carbobenzyloxy)-4-piperidone (3.99 g) in dry tetrahydrofuran (17 mL). The reaction mixture is stirred for three hours, during which the reaction temperature is allowed to rise to 0° C., and is quenched with saturated aqueous ammonium chloride (30 mL). The mixture is then diluted with water (100 mL), the layers are separated, the aqueous phase is extracted with diethyl ether, and the combined organic phase is washed with saline (50 mL), dried over anhydrous sodium sulfate, and concentrated under reduced pressure. The residue is chromato-graphed on silica gel (230-400 mesh, 350 g), eluting with ethyl acetate/hexane (25/75), and those fractions with an Rf =0.38 by TLC (ethyl acetate/hexane, 50/50) are pooled and con-centrated under reduced pressure to give the title compound, mp 156° C.-158° C. The reaction mixture is stirred for three hours, during which the reaction temperature to rise to 0° C. is quenched with saturated aqueous ammonium chloride (30 mL) The mixture is then diluted with water (100 mL) the layers are separated the aqueous phase is extracted with diethyl ether the combined organic phase is washed with saline (50 mL) dried over anhydrous sodium sulfate concentrated under reduced pressure eluting with ethyl acetate/hexane (25/75)

Conditions: temp:-78.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: Benzyl 4-bromophenylcarbamate (20 g, 65.3 mmol) was taken in anhydrous THF (440 mL) and cooled to −78° C. To this solution, n-BuLi (55 mL, 137.2 mmol) was added dropwise and stirred for 0.5 h at −78° C. To this mixture, DMF (7.6 mL) was added dropwise and the reaction was allowed to warm to room temperature over a period of 5 h. The reaction mixture was quenched with 1 N HCl and then concentrated to remove THF, followed by addition of water. The mixture was extracted with three portions of ethyl acetate. The combined organic phases were washed with H2O, brine, and dried (MgSO4) filtered and concentrated. Trituration with hexanes and then with 20% ethyl acetate in hexanes afforded the title compound as a yellow solid. to warm to room temperature over a period of 5 h The reaction mixture was quenched with 1 N HCl concentrated to remove THF followed by addition of water The mixture was extracted with three portions of ethyl acetate The combined organic phases were washed with H2O, brine dried (MgSO4) filtered concentrated

Conditions: temp:-78.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: To a solution of N-(carbobenzyloxy)-4-bromoaniline (5.00 g) in dry tetrahydrofuran (80 mL) at -78° C. under N2 is added n-butyllithium (21.4 mL, 1.6M in hexanes) dropwise over five minutes. The resulting yellow solution is stirred at -78° C. for 30 minutes and is then treated with a solution of N-(carbobenzyloxy)-4-piperidone (3.99 g) in dry tetrahydrofuran (17 mL). The reaction mixture is stirred for three hours, during which the reaction temperature is allowed to rise to 0° C., and is quenched with saturated aqueous ammonium chloride (30 mL). The mixture is then diluted with water (100 mL), the layers are separated, the aqueous phase is extracted with diethyl ether, and the combined organic phase is washed with saline (50 mL), dried over anhydrous sodium sulfate, and concentrated under reduced pressure. The residue is chromato-graphed on silica gel (230-400 mesh, 350 g), eluting with ethyl acetate/hexane (25/75), and those fractions with an Rf =0.38 by TLC (ethyl acetate/hexane, 50/50) are pooled and con-centrated under reduced pressure to give the title compound, mp 156° C.-158° C. The reaction mixture is stirred for three hours, during which the reaction temperature to rise to 0° C. is quenched with saturated aqueous ammonium chloride (30 mL) The mixture is then diluted with water (100 mL) the layers are separated the aqueous phase is extracted with diethyl ether the combined organic phase is washed with saline (50 mL) dried over anhydrous sodium sulfate concentrated under reduced pressure eluting with ethyl acetate/hexane (25/75)

Conditions: temp:-78.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: To a solution of N-(carbobenzyloxy)-4-bromoaniline (5.00 g) in dry tetrahydrofuran (80 mL) at −78° C. under N2 is added n-butyllithium (21.4 mL, 1.6 M in hexanes) dropwise over five minutes. The resulting yellow solution is stirred at −78° C. for 30 minutes and is then treated with a solution of N-(carbobenzyloxy)-4-piperidone (3.99 g) in dry tetrahydrofuran (17 mL). The reaction mixture is stirred for three hours, during which the reaction temperature is allowed to rise to 0° C., and is quenched with saturated aqueous ammonium chloride (30 mL). The mixture is then diluted with water (100 mL), the layers are separated, the aqueous phase is extracted with diethyl ether, and the combined organic phase is washed with saline (50 mL), dried over anhydrous sodium sulfate, and concentrated under reduced pressure. The residue is chromato-graphed on silica gel (230-400 mesh, 350 g), eluting with ethyl acetate/hexane (25/75), and those fractions with an Rf=0.38 by TLC (ethyl acetate/hexane, 50/50) are pooled and con-centrated under reduced pressure by give the title compound, mp 156° C.-158° C. The reaction mixture is stirred for three hours, during which the reaction temperature to rise to 0° C. is quenched with saturated aqueous ammonium chloride (30 mL) The mixture is then diluted with water (100 mL) the layers are separated the aqueous phase is extracted with diethyl ether the combined organic phase is washed with saline (50 mL) dried over anhydrous sodium sulfate concentrated under reduced pressure eluting with ethyl acetate/hexane (25/75)