ISOPROPYL-(4-METHOXY-BENZYL)-AMINE

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

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

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

Procedure: A mixture of 4-methoxybenzylamine (1.37 g, 10 mmol) and acetone (0.81 mL, 11 mmol) in dry dichloroethane (20 mL) were stirred at room temperature for 30 minutes. To the solution was added sodium triacetoxyborohydride (3.18 g, 15 mmol) and the resulting mixture was stirred at room temperature for 17 hours. The reaction mixture was quenched with 1 N NaOH (50 mL) and the layers were separated. The aqueous layer was extracted with dichloromethane (2×20 mL). The combined extracts were washed with water (20 mL), brine (20 mL), dried over MgSO4, filtered through Celite, and concentrated under reduced pressure. The residue was chromatographed eluting with 10% MeOH in dichloromethane with 1% triethylamine to provide 1.53 g of oil (85% yield). the resulting mixture was stirred at room temperature for 17 hours The reaction mixture was quenched with 1 N NaOH (50 mL) the layers were separated The aqueous layer was extracted with dichloromethane (2×20 mL) The combined extracts were washed with water (20 mL), brine (20 mL) dried over MgSO4 filtered through Celite concentrated under reduced pressure The residue was chromatographed eluting with 10% MeOH in dichloromethane with 1% triethylamine

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

Procedure: 10A was prepared from a mixture of 1F and N-(4-methoxybenzyl)propan-2-amine following the procedure employed for the preparation of 1G. HPLC: Rt=4.27 min. (YMC S5 ODS 4.6×50 mm, 10-90% aqueous methanol containing 0.2% H3PO4, 4 min. gradient, monitored at 220 nm). MS (ES): m/z=356.1 [M+H]+.

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

Procedure: 10A was prepared from a mixture of 1F and N-(4-methoxybenzyl)propan-2-amine following the procedure employed for the preparation of 1G. HPLC: Rt=4.27 min. (YMC S5 ODS 4.6×50 mm, 10-90% aqueous methanol containing 0.2% H3PO4, 4 min. gradient, monitored at 220 nm). MS (ES): m/z=356.1 [M+H]+.

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

Procedure: A mixture of 4-methoxybenzylamine (1.37 g, 10 mmol) and acetone (0.81 mL, 11 mmol) in dry dichloroethane (20 mL) were stirred at room temperature for 30 minutes. To the solution was added sodium triacetoxyborohydride (3.18 g, 15 mmol) and the resulting mixture was stirred at room temperature for 17 hours. The reaction mixture was quenched with 1 N NaOH (50 mL) and the layers were separated. The aqueous layer was extracted with dichloromethane (2×20 mL). The combined extracts were washed with water (20 mL), brine (20 mL), dried over MgSO4, filtered through Celite, and concentrated under reduced pressure. The residue was chromatographed eluting with 10% MeOH in dichloromethane with 1% triethylamine to provide 1.53 g of oil (85% yield). the resulting mixture was stirred at room temperature for 17 hours The reaction mixture was quenched with 1 N NaOH (50 mL) the layers were separated The aqueous layer was extracted with dichloromethane (2×20 mL) The combined extracts were washed with water (20 mL), brine (20 mL) dried over MgSO4 filtered through Celite concentrated under reduced pressure The residue was chromatographed eluting with 10% MeOH in dichloromethane with 1% triethylamine

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

Procedure: A mixture of 4-methoxybenzylamine (1.37 g, 10 mmol) and acetone (0.81 mL, 11 mmol) in dry dichloroethane (20 mL) were stirred at room temperature for 30 minutes. To the solution was added sodium triacetoxyborohydride (3.18 g, 15 mmol) and the resulting mixture was stirred at room temperature for 17 hours. The reaction mixture was quenched with 1 N NaOH (50 mL) and the layers were separated. The aqueous layer was extracted with dichloromethane (2×20 mL). The combined extracts were washed with water (20 mL), brine (20 mL), dried over MgSO4, filtered through Celite, and concentrated under reduced pressure. The residue was chromatographed eluting with 10% MeOH in dichloromethane with 1% triethylamine to provide 1.53 g of oil (85% yield). the resulting mixture was stirred at room temperature for 17 hours The reaction mixture was quenched with 1 N NaOH (50 mL) the layers were separated The aqueous layer was extracted with dichloromethane (2×20 mL) The combined extracts were washed with water (20 mL), brine (20 mL) dried over MgSO4 filtered through Celite concentrated under reduced pressure The residue was chromatographed eluting with 10% MeOH in dichloromethane with 1% triethylamine

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

Procedure: A mixture of 4-methoxybenzylamine (1.37 g, 10 mmol) and acetone (0.81 mL, 11 mmol) in dry dichloroethane (20 mL) were stirred at room temperature for 30 minutes. To the solution was added sodium triacetoxyborohydride (3.18 g, 15 mmol) and the resulting mixture was stirred at room temperature for 17 hours. The reaction mixture was quenched with 1 N NaOH (50 mL) and the layers were separated. The aqueous layer was extracted with dichloromethane (2×20 mL). The combined extracts were washed with water (20 mL), brine (20 mL), dried over MgSO4, filtered through Celite, and concentrated under reduced pressure. The residue was chromatographed eluting with 10% MeOH in dichloromethane with 1% triethylamine to provide 1.53 g of oil (85% yield). the resulting mixture was stirred at room temperature for 17 hours The reaction mixture was quenched with 1 N NaOH (50 mL) the layers were separated The aqueous layer was extracted with dichloromethane (2×20 mL) The combined extracts were washed with water (20 mL), brine (20 mL) dried over MgSO4 filtered through Celite concentrated under reduced pressure The residue was chromatographed eluting with 10% MeOH in dichloromethane with 1% triethylamine

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

Procedure: A mixture of 4-methoxybenzylamine (1.37 g, 10 mmol) and acetone (0.81 mL, 11 mmol) in dry dichloroethane (20 mL) were stirred at room temperature for 30 minutes. To the solution was added sodium triacetoxyborohydride (3.18 g, 15 mmol) and the resulting mixture was stirred at room temperature for 17 hours. The reaction mixture was quenched with 1 N NaOH (50 mL) and the layers were separated. The aqueous layer was extracted with dichloromethane (2×20 mL). The combined extracts were washed with water (20 mL), brine (20 mL), dried over MgSO4, filtered through Celite, and concentrated under reduced pressure. The residue was chromatographed eluting with 10% MeOH in dichloromethane with 1% triethylamine to provide 1.53 g of oil (85% yield). the resulting mixture was stirred at room temperature for 17 hours The reaction mixture was quenched with 1 N NaOH (50 mL) the layers were separated The aqueous layer was extracted with dichloromethane (2×20 mL) The combined extracts were washed with water (20 mL), brine (20 mL) dried over MgSO4 filtered through Celite concentrated under reduced pressure The residue was chromatographed eluting with 10% MeOH in dichloromethane with 1% triethylamine

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

Procedure: 10A was prepared from a mixture of 1F and N-(4-methoxybenzyl)propan-2-amine following the procedure employed for the preparation of 1G. HPLC: Rt=4.27 min. (YMC S5 ODS 4.6×50 mm, 10-90% aqueous methanol containing 0.2% H3PO4, 4 min. gradient, monitored at 220 nm). MS (ES): m/z=356.1 [M+H]+.