腐胺盐酸盐（1,4-丁二胺二盐酸盐）

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

实验步骤: 1,4-butanediamine dihydrochloride (5.96 g, 37 mmol) was dissolved in water (15 mL), and DMF (50 mL) was added. With rapid stirring, CBZ-Cl (1.0 mL, 7.0 mmol) was added dropwise over 2 minutes. The cloudy solution had pH~2.8. The pH was adjusted to 9.0 with 5N NaOH, (clear solution) and stirred for 2 hr. The reaction mixture was acidified to pH=1.25, extracted with ether (2×), made basic (pH>10) with 5N NaOH, and extracted with dichloromethane (2×). The dichloromethane fractions were combined and washed with water (2×), dried and evaporated in vacuo to provide the crude mono-CBZ amine (0.72 g, 3.24 mmol, 46%) which was used as is in the next step. extracted with ether (2×) extracted with dichloromethane (2×) washed with water (2×) dried evaporated in vacuo

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

实验步骤: 1,4-butanediamine dihydrochloride (5.96 g, 37 mmol) was dissolved in water (15 mL), and DMF (50 mL) was added. With rapid stirring, CBZ-Cl (1.0 mL, 7.0 mmol) was added dropwise over 2 minutes. The cloudy solution had pH~2.8. The pH was adjusted to 9.0 with 5N NaOH, (clear solution) and stirred for 2 hr. The reaction mixture was acidified to pH=1.25, extracted with ether (2×), made basic (pH>10) with 5N NaOH, and extracted with dichloromethane (2×). The dichloromethane fractions were combined and washed with water (2×), dried and evaporated in vacuo to provide the crude mono-CBZ amine (0.72 g, 3.24 mmol, 46%) which was used as is in the next step. extracted with ether (2×) extracted with dichloromethane (2×) washed with water (2×) dried evaporated in vacuo

反应条件: temp:110.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

实验步骤: 1,4-Diaminobutane dihydrochloride (0.97 g; 6 mmol), sodium t-butoxide (1.87 g, 19.5 mmol), rac-BINAP (61.0 mg, 0.09 mmol), and Pd(dba)2 (35.0 mg, 0.06 mmol) are charged to a flame dried screw-cap vial. The vial is vacuumed and back filled with nitrogen. Then anhydrous toluene (15 mL) is added, followed by the addition of 1-bromo-2,4-difluorobenzene (0.34 mL, 3.00 mmol). The mixture is stirred under nitrogen at 110° C. overnight. The reaction mixture is diluted with 80 mL of diethyl ether and filtered through a pad of celite 545. The filtrate is extracted with 6N aqueous HCl (10 mL×3). The combined aqueous layers are washed twice with diethyl ether and adjusted with 1M aqueous NaOH to pH>12. The aqueous layer was extracted with diethyl ether three times. The combined ether phase is dried over anhydrous Na2SO4, filtered, and concentrated to obtain N′-(2,4-difluorophenyl)butane-1,4-diamine as a brown oil: 1H NMR (CDCl3) δ 1.55 (m, 2H), 1.66 (m, 2H), 2.74 (t, 2H), 3.12 (t, 2H), 6.55 (m, 1H), 6.73 (m, 2H). dried screw-cap vial back filled with nitrogen Then anhydrous toluene (15 mL) is added filtered through a pad of celite 545 The filtrate is extracted with 6N aqueous HCl (10 mL×3) The combined aqueous layers are washed twice with diethyl ether The aqueous layer was extracted with diethyl ether three times The combined ether phase is dried over anhydrous Na2SO4 filtered concentrated

反应条件: temp:110.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

实验步骤: 1,4-Diaminobutane dihydrochloride (0.97 g, 6 mmol), sodium t-butoxide (1.87 g, 19.5 mmol), rac-BINAP (61.0 mg, 0.09 mmol), and Pd(dba)2 (35.0 mg, 0.06 mmol) are charged to a flame dried screw-cap vial. The vial is vacuumed and back filled with nitrogen. Then anhydrous toluene (15 mL) is added, followed by the addition of 1-bromo-2,4-difluorobenzene (0.34 mL, 3.00 mmol). The mixture is stirred under nitrogen at 110° C. overnight. The reaction mixture is diluted with 80 mL of diethyl ether and filtered through a pad of celite 545. The filtrate is extracted with 6N aqueous HCl (10 mL×3). The combined aqueous layers are washed twice with diethyl ether and adjusted with 1M aqueous NaOH to pH>12. The aqueous layer was extracted with diethyl ether three times. The combined ether phase is dried over anhydrous Na2SO4, filtered, and concentrated to obtain N′-(2,4-difluorophenyl)butane-1,4-diamine as a brown oil: 1H NMR (CDCl3) δ 1.55 (m, 2H), 1.66 (m, 2H), 2.74 (t, 2H), 3.12 (t, 2H), 6.55 (m, 1 H), 6.73 (m, 2H). dried screw-cap vial back filled with nitrogen Then anhydrous toluene (15 mL) is added filtered through a pad of celite 545 The filtrate is extracted with 6N aqueous HCl (10 mL×3) The combined aqueous layers are washed twice with diethyl ether The aqueous layer was extracted with diethyl ether three times The combined ether phase is dried over anhydrous Na2SO4 filtered concentrated

反应条件: temp:110.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

实验步骤: 1,4-Diaminobutane dihydrochloride (0.97 g, 6 mmol), sodium t-butoxide (1.87 g, 19.5 mmol), rac-BINAP (61.0 mg, 0.09 mmol), and Pd(dba)2 (35.0 mg, 0.06 mmol) are charged to a flame dried screw-cap vial. The vial is vacuumed and back filled with nitrogen. Then anhydrous toluene (15 mL) is added, followed by the addition of 1-bromo-2,4-difluorobenzene (0.34 mL, 3.00 mmol). The mixture is stirred under nitrogen at 110° C. overnight. The reaction mixture is diluted with 80 mL of diethyl ether and filtered through a pad of celite 545. The filtrate is extracted with 6N aqueous HCl (10 mL×3). The combined aqueous layers are washed twice with diethyl ether and adjusted with 1M aqueous NaOH to pH>12. The aqueous layer was extracted with diethyl ether three times. The combined ether phase is dried over anhydrous Na2SO4, filtered, and concentrated to obtain N′-(2,4-difluorophenyl)butane-1,4-diamine as a brown oil: 1H NMR (CDCl3) δ 1.55 (m, 2H), 1.66 (m, 2H), 2.74 (t, 2H), 3.12 (t, 2H), 6.55 (m, 1 H), 6.73 (m, 2H). dried screw-cap vial back filled with nitrogen Then anhydrous toluene (15 mL) is added filtered through a pad of celite 545 The filtrate is extracted with 6N aqueous HCl (10 mL×3) The combined aqueous layers are washed twice with diethyl ether The aqueous layer was extracted with diethyl ether three times The combined ether phase is dried over anhydrous Na2SO4 filtered concentrated

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

实验步骤: 1,4-butanediamine dihydrochloride (5.96 g, 37 mmol) was dissolved in water (15 mL), and DMF (50 mL) was added. With rapid stirring, CBZ-Cl (1.0 mL, 7.0 mmol) was added dropwise over 2 minutes. The cloudy solution had pH~2.8. The pH was adjusted to 9.0 with 5 N NaOH, (clear solution) and stirred for 2 hr. 10 The reaction mixture was acidified to pH=1.25, extracted with ether (2 X), made basic (pH>10) with 5 N NaOH, and extracted with dichloromethane (2 X). The dichloromethane fractions were combined and washed with water (2 X), dried and evaporated in vacuo to provide the crude mono-CBZ amine (0.72 g, 3.24 mmol, 46%) which was used as is in the next step. extracted with ether (2 X) extracted with dichloromethane (2 X) washed with water (2 X) dried evaporated in vacuo

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

实验步骤: 1,4-butanediamine dihydrochloride (5.96 g, 37 mmol) was dissolved in water (15 mL), and DMF (50 mL) was added. With rapid stirring, CBZ-Cl (1.0 mL, 7.0 mmol) was added dropwise over 2 minutes. The cloudy solution had pH ~2.8. The pH was adjusted to 9.0 with 5 E NaOH, (clear solution) and stirred for 2 hr. The reaction mixture was acidified to pH=1.25, extracted with ether (2×), made basic (pH>10) with 5 N NaOH, and extracted with dichloromethane (2×). The dichloromethane fractions were combined and washed with water (2×), dried and evaporated in vacuo to provide the crude mono-CBZ amine (0.72 g, 3.24 mmol, 46%) which was used as is in the next step. extracted with ether (2×) extracted with dichloromethane (2×) washed with water (2×) dried evaporated in vacuo

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

实验步骤: 1,4-butanediamine dihydrochloride (5.96 g, 37 mmol) was dissolved in water (15 mL), and DMF (50 mL) was added. With rapid stirring, CBZ-Cl (1.0 mL, 7.0 mmol) was added dropwise over 2 minutes. The cloudy solution had pH~2.8. The pH was adjusted to 9.0 with 5N NaOH, (clear solution) and stirred for 2 hr. The reaction mixture was acidified to pH=1.25, extracted with ether (2×), made basic (pH>10) with 5N NaOH, and extracted with dichloromethane (2×). The dichloromethane fractions were combined and washed with water (2×), dried and evaporated in vacuo to provide the crude mono-CBZ amine (0.72 g, 3.24 mmol, 46%) which was used as is in the next step. extracted with ether (2×) extracted with dichloromethane (2×) washed with water (2×) dried evaporated in vacuo

反应条件: temp:110.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

实验步骤: 1,4-Diaminobutane dihydrochloride (0.97 g; 6 mmol), sodium t-butoxide (1.87 g, 19.5 mmol), rac-BINAP (61.0 mg, 0.09 mmol), and Pd(dba)2 (35.0 mg, 0.06 mmol) are charged to a flame dried screw-cap vial. The vial is vacuumed and back filled with nitrogen. Then anhydrous toluene (15 mL) is added, followed by the addition of 1-bromo-2,4-difluorobenzene (0.34 mL, 3.00 mmol). The mixture is stirred under nitrogen at 110° C. overnight. The reaction mixture is diluted with 80 mL of diethyl ether and filtered through a pad of celite 545. The filtrate is extracted with 6N aqueous HCl (10 mL×3). The combined aqueous layers are washed twice with diethyl ether and adjusted with 1M aqueous NaOH to pH>12. The aqueous layer was extracted with diethyl ether three times. The combined ether phase is dried over anhydrous Na2SO4, filtered, and concentrated to obtain N′-(2,4-difluorophenyl)butane-1,4-diamine as a brown oil: 1H NMR (CDCl3) δ 1.55 (m, 2H), 1.66 (m, 2H), 2.74 (t, 2H), 3.12 (t, 2H), 6.55 (m, 1H), 6.73 (m, 2H). dried screw-cap vial back filled with nitrogen Then anhydrous toluene (15 mL) is added filtered through a pad of celite 545 The filtrate is extracted with 6N aqueous HCl (10 mL×3) The combined aqueous layers are washed twice with diethyl ether The aqueous layer was extracted with diethyl ether three times The combined ether phase is dried over anhydrous Na2SO4 filtered concentrated