1-(4-bromophenyl)-2-pyrrolidin-1-ylethanone

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

Procedure: Diisopropylethylamine (6.2 mL, 36.0 mmol) and pyrrolidine (2.3 mL, 27.6 mmol) were added to a THF (90 mL) solution of 2-bromo-1-(4-bromophenyl)ethanone (5.0 g, 18.0 mmol), and stirred at room temperature for 2 hours. Saturated sodium bicarbonate water was added to the reaction liquid, extracted with chloroform, and dried with anhydrous magnesium sulfate. The solvent was concentrated under reduced pressure and the obtained residue was purified by silica gel column chromatography (C-200, methanol:chloroform=1:99 to 3:97) to obtain the entitled compound (2.35 g, 49%). extracted with chloroform dried with anhydrous magnesium sulfate The solvent was concentrated under reduced pressure the obtained residue was purified by silica gel column chromatography (C-200, methanol:chloroform=1:99 to 3:97)

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

Procedure: Diisopropylethylamine (6.2 mL, 36.0 mmol) and pyrrolidine (2.3 mL, 27.6 mmol) were added to a THF (90 mL) solution of 2-bromo-1-(4-bromophenyl)ethanone (5.0 g, 18.0 mmol), and stirred at room temperature for 2 hours. Saturated sodium bicarbonate water was added to the reaction liquid, extracted with chloroform, and dried with anhydrous magnesium sulfate. The solvent was concentrated under reduced pressure and the obtained residue was purified by silica gel column chromatography (C-200, methanol:chloroform=1:99 to 3:97) to obtain the entitled compound (2.35 g, 49%). extracted with chloroform dried with anhydrous magnesium sulfate The solvent was concentrated under reduced pressure the obtained residue was purified by silica gel column chromatography (C-200, methanol:chloroform=1:99 to 3:97)

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

Procedure: Diisopropylethylamine (6.2 mL, 36.0 mmol) and pyrrolidine (2.3 mL, 27.6 mmol) were added to a THF (90 mL) solution of 2-bromo-1-(4-bromophenyl)ethanone (5.0 g, 18.0 mmol), and stirred at room temperature for 2 hours. Saturated sodium bicarbonate water was added to the reaction liquid, extracted with chloroform, and dried with anhydrous magnesium sulfate. The solvent was concentrated under reduced pressure and the obtained residue was purified by silica gel column chromatography (C-200, methanol:chloroform=1:99 to 3:97) to obtain the entitled compound (2.35 g, 49%). extracted with chloroform dried with anhydrous magnesium sulfate The solvent was concentrated under reduced pressure the obtained residue was purified by silica gel column chromatography (C-200, methanol:chloroform=1:99 to 3:97)

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

Procedure: 1-(4-Bromophenyl)-2-(1-pyrrolidinyl)ethanone (4.45 g, 16.6 mmol) and methyl amine (33 mL, 66.4 mmol of 2 M solution in THF) were dissolved in 75 mL THF and maintained for 15 minutes at room temperature. NaBH3CN (3.13 g, 49.8 mmol) was added and the reaction mixture was treated with 1 mL acetic acid and stirred at room temperature for 4 days. The solvent was removed under reduced pressure. The residue was dissolved in 100 mL of EtOAc and washed with sodium bicarbonate (100 mL) and then brine (100 mL). The organic layer was dried over Na2SO4, filtered, and concentrated under reduced pressure to give 4.7 g (99%) of the title compound as a yellow oil. MS (ES) m/e 284 [M+H]+. The solvent was removed under reduced pressure The residue was dissolved in 100 mL of EtOAc washed with sodium bicarbonate (100 mL) The organic layer was dried over Na2SO4 filtered concentrated under reduced pressure

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

Procedure: 1-(4-Bromophenyl)-2-(1-pyrrolidinyl)ethanone (4.45 g, 16.6 mmol) and methyl amine (33 mL, 66.4 mmol of 2 M solution in THF) were dissolved in 75 mL THF and maintained for 15 minutes at room temperature. NaBH3CN (3.13 g, 49.8 mmol) was added and the reaction mixture was treated with 1 mL acetic acid and stirred at room temperature for 4 days. The solvent was removed under reduced pressure. The residue was dissolved in 100 mL of EtOAc and washed with sodium bicarbonate (100 mL) and then brine (100 mL). The organic layer was dried over Na2SO4, filtered, and concentrated under reduced pressure to give 4.7 g (99%) of the title compound as a yellow oil. MS (ES) m/e 284 [M+H]+. The solvent was removed under reduced pressure The residue was dissolved in 100 mL of EtOAc washed with sodium bicarbonate (100 mL) The organic layer was dried over Na2SO4 filtered concentrated under reduced pressure

Conditions: temp:0.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: 2-bromo-1-(4-bromophenyl)ethanone (5.0 g, 18 mmol) was dissolved in 10 mL diethyl ether and added dropwise over 15 min to a solution of pyrrolidine (3.0 mL, 36 mmol) in 20 mL diethyl ether cooled to 0° C. in an ice bath. The resulting solution was allowed to warm to room temperature and maintained for 1 h. The solvent was removed under reduced pressure. The residue was dissolved in 100 mL of EtOAc and washed with sodium bicarbonate (100 mL) and then brine (100 mL). The organic layer was dried over Na2SO4, filtered, and concentrated under reduced pressure to give 4.6 g (96%) of the title compound as a yellow/orange solid. MS (ES) m/e 268/270 [M+H]+. to warm to room temperature maintained for 1 h The solvent was removed under reduced pressure The residue was dissolved in 100 mL of EtOAc washed with sodium bicarbonate (100 mL) The organic layer was dried over Na2SO4 filtered concentrated under reduced pressure

Conditions: temp:0.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: 2-bromo-1-(4-bromophenyl)ethanone (5.0 g, 18 mmol) was dissolved in 10 mL diethyl ether and added dropwise over 15 min to a solution of pyrrolidine (3.0 mL, 36 mmol) in 20 mL diethyl ether cooled to 0° C. in an ice bath. The resulting solution was allowed to warm to room temperature and maintained for 1 h. The solvent was removed under reduced pressure. The residue was dissolved in 100 mL of EtOAc and washed with sodium bicarbonate (100 mL) and then brine (100 mL). The organic layer was dried over Na2SO4, filtered, and concentrated under reduced pressure to give 4.6 g (96%) of the title compound as a yellow/orange solid. MS (ES) m/e 268/270 [M+H]+. to warm to room temperature maintained for 1 h The solvent was removed under reduced pressure The residue was dissolved in 100 mL of EtOAc washed with sodium bicarbonate (100 mL) The organic layer was dried over Na2SO4 filtered concentrated under reduced pressure

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

Procedure: 1-(4-Bromophenyl)-2-(1-pyrrolidinyl)ethanone (4.45 g, 16.6 mmol) and methyl amine (33 mL, 66.4 mmol of 2 M solution in THF) were dissolved in 75 mL THF and maintained for 15 minutes at room temperature. NaBH3CN (3.13 g, 49.8 mmol) was added and the reaction mixture was treated with 1 mL acetic acid and stirred at room temperature for 4 days. The solvent was removed under reduced pressure. The residue was dissolved in 100 mL of EtOAc and washed with sodium bicarbonate (100 mL) and then brine (100 mL). The organic layer was dried over Na2SO4, filtered, and concentrated under reduced pressure to give 4.7 g (99%) of the title compound as a yellow oil. MS (ES) m/e 284 [M+H]+. The solvent was removed under reduced pressure The residue was dissolved in 100 mL of EtOAc washed with sodium bicarbonate (100 mL) The organic layer was dried over Na2SO4 filtered concentrated under reduced pressure

Conditions: temp:0.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: 2-bromo-1-(4-bromophenyl)ethanone (5.0 g, 18 mmol) was dissolved in 10 mL diethyl ether and added dropwise over 15 min to a solution of pyrrolidine (3.0 mL, 36 mmol) in 20 mL diethyl ether cooled to 0° C. in an ice bath. The resulting solution was allowed to warm to room temperature and maintained for 1 h. The solvent was removed under reduced pressure. The residue was dissolved in 100 mL of EtOAc and washed with sodium bicarbonate (100 mL) and then brine (100 mL). The organic layer was dried over Na2SO4, filtered, and concentrated under reduced pressure to give 4.6 g (96%) of the title compound as a yellow/orange solid. MS (ES) m/e 268/270 [M+H]+. to warm to room temperature maintained for 1 h The solvent was removed under reduced pressure The residue was dissolved in 100 mL of EtOAc washed with sodium bicarbonate (100 mL) The organic layer was dried over Na2SO4 filtered concentrated under reduced pressure

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

Procedure: Diisopropylethylamine (6.2 mL, 36.0 mmol) and pyrrolidine (2.3 mL, 27.6 mmol) were added to a THF (90 mL) solution of 2-bromo-1-(4-bromophenyl)ethanone (5.0 g, 18.0 mmol), and stirred at room temperature for 2 hours. Saturated sodium bicarbonate water was added to the reaction liquid, extracted with chloroform, and dried with anhydrous magnesium sulfate. The solvent was concentrated under reduced pressure and the obtained residue was purified by silica gel column chromatography (C-200, methanol:chloroform=1:99 to 3:97) to obtain the entitled compound (2.35 g, 49%). extracted with chloroform dried with anhydrous magnesium sulfate The solvent was concentrated under reduced pressure the obtained residue was purified by silica gel column chromatography (C-200, methanol:chloroform=1:99 to 3:97)