2-(1-phenylethylamino)ethanol

反応条件: temp:0.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

実験手順: 100 g (605.32 mmole) of N-(2-hydroxyethyl)-α-methylbenzylamine produced in Example 5(1) above was suspended in 515 ml of 48% aqueous hydrobromic acid solution and the resulting suspension was reacted at 126° C. for 30 minutes under refluxing. The reaction solution was then distilled for 2 hours under normal pressure at constant temperature and 465 ml of aqueous hydrobromic acid and water, the reaction by-product, was removed. The residue was dissolved in 550 ml of acetone, and 500 ml of ethyl acetate and 670 ml of ether were added thereto. The reaction solution was stirred for 30 minutes, cooled to 0° C. and then allowed to stand for 3 hours. The resulting solid product was filtered, washed with 400 ml of ethyl acetate and then dried to obtain 97 g of the first crop of the title compound. The filtrate was then concentrated. The residue was dissolved in 450 ml of acetone, diluted with 680 ml of ether and then allowed to stand at 0° C. for 12 hours. The resulting solid product was filtered, collected, and washed with 450 ml of ethyl acetate to obtain 32.5 g of the second crop of the title compound. the resulting suspension was reacted at 126° C. for 30 minutes under refluxing The reaction solution was then distilled for 2 hours under normal pressure at constant temperature and 465 ml of aqueous hydrobromic acid and water the reaction by-product, was removed The residue was dissolved in 550 ml of acetone 500 ml of ethyl acetate and 670 ml of ether were added to stand for 3 hours The resulting solid product was filtered washed with 400 ml of ethyl acetate dried

反応条件: temp:0.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

実験手順: 100 g (605.32 mmole) of N-(2-hydroxyethyl)-α-methylbenzylamine produced in Example 5(1) above was suspended in 515 ml of 48% aqueous hydrobromic acid solution and the resulting suspension was reacted at 126° C. for 30 minutes under refluxing. The reaction solution was then distilled for 2 hours under normal pressure at constant temperature and 465 ml of aqueous hydrobromic acid and water, the reaction by-product, was removed. The residue was dissolved in 550 ml of acetone, and 500 ml of ethyl acetate and 670 ml of ether were added thereto. The reaction solution was stirred for 30 minutes, cooled to 0° C. and then allowed to stand for 3 hours. The resulting solid product was filtered, washed with 400 ml of ethyl acetate and then dried to obtain 97 g of the first crop of the title compound. The filtrate was then concentrated. The residue was dissolved in 450 ml of acetone, diluted with 680 ml of ether and then allowed to stand at 0° C. for 12 hours. The resulting solid product was filtered, collected, and washed with 450 ml of ethyl acetate to obtain 32.5 g of the second crop of the title compound. the resulting suspension was reacted at 126° C. for 30 minutes under refluxing The reaction solution was then distilled for 2 hours under normal pressure at constant temperature and 465 ml of aqueous hydrobromic acid and water the reaction by-product, was removed The residue was dissolved in 550 ml of acetone 500 ml of ethyl acetate and 670 ml of ether were added to stand for 3 hours The resulting solid product was filtered washed with 400 ml of ethyl acetate dried

反応条件: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

実験手順: To a stirred solution of 2-(1-phenylethylamino)ethanol (33) (2.71 g, 16.4 mmol, Eq: 1.00) in dichloromethane (60 ml) were added diisopropylethylamine (2.97 g, 4.01 ml, 23.0 mmol, Eq: 1.4) followed by tert-butyldimethylsilyl chloride (2.72 g, 18.0 mmol, Eq: 1.1) at room temperature under nitrogen atmosphere. The resulting solution was stirred for 16 hrs and then it was poured into water (200 ml). The organic layer was separated, washed with brine, and dried with MgSO4, concentrated, and chromatographed (silica gel, gradient 0 to 10% ethyl acetate-hexane) to obtain 2-(tert-butyldimethylsilyloxy)-N-(1-phenylethyl)ethanamine (34) (oil, 3.75 g, 13.4 mmol, 81.8% yield). The organic layer was separated washed with brine dried with MgSO4 concentrated chromatographed (silica gel, gradient 0 to 10% ethyl acetate-hexane)

反応条件: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

実験手順: A mixture of acetophenone (2.00 g, 16.6 mmol, Eq: 1.00), 2-aminoethanol (3.05 g, 49.9 mmol, Eq: 3.00) and titanium(IV) isopropoxide (6.15 g, 6.41 ml, 21.6 mmol, Eq: 1.3) in absolute methanol (25 ml) was stirred under nitrogen at room temperature for 48 hrs. Sodium borohydride (630 mg, 16.6 mmol, Eq: 1.00) was then added at 0° C. and the resulting mixture was stirred for an additional 2 hr. The reaction was then quenched by adding water (1 ml). Stirring was continued at room temperature for 20 min., then the reaction mixture was acidified with 1N HCl. After filtration over a pad of Celite, washing with ethyl acetate, any drying over magnesium sulfate, the mixture was concentrated to obtain 2-(1-phenylethylamino)ethanol (oil, 2.71 g, 16.4 mmol, 98.5% yield). the resulting mixture was stirred for an additional 2 hr The reaction was then quenched by adding water (1 ml) Stirring was continued at room temperature for 20 min. After filtration over a pad of Celite washing with ethyl acetate any drying over magnesium sulfate, the mixture was concentrated

反応条件: temp:0.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

実験手順: 100 g(605.32 mmole) of N-(2-hydroxyethyl)-α-methylbenzylamine produced in Example 5(1) above was suspended in 515 ml of 48% aqueous hydrobromic acid solution and the resulting suspension was reacted at 126° C. for 30 minutes under refluxing. The reaction solution was then distilled for 2 hours under normal pressure at constant temperature and 465 ml of aqueous hydrobromic acid and water, the reaction by-product, was removed. The residue was dissolved in 550 ml of acetone, and 500 ml of ethyl acetate and 670 ml of ether were added thereto. The reaction solution was stirred for 30 minutes, cooled to 0° C. and then allowed to stand for 3 hours. The resulting solid product was filtered, washed with 400 ml of ethyl acetate and then dried to obtain 97 g of the first crop of the title compound. The filtrate was then concentrated. The residue was dissolved in 450 ml of acetone, diluted with 680 ml of ether and then allowed to stand at 0° C. for 12 hours. The resulting solid product was filtered, collected, and washed with 450 ml of ethyl acetate to obtain 32.5 g of the second crop of the title compound. the resulting suspension was reacted at 126° C. for 30 minutes under refluxing The reaction solution was then distilled for 2 hours under normal pressure at constant temperature and 465 ml of aqueous hydrobromic acid and water the reaction by-product, was removed The residue was dissolved in 550 ml of acetone 500 ml of ethyl acetate and 670 ml of ether were added to stand for 3 hours The resulting solid product was filtered washed with 400 ml of ethyl acetate dried

反応条件: temp:0.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

実験手順: 100 g (605.32 mmole) of N-(2-hydroxyethyl)-α-methylbenzylamine produced in Example 5(1) above was suspended in 515 ml of 48% aqueous hydrobromic acid solution and the resulting suspension was reacted at 126° C. for 30 minutes under refluxing. The reaction solution was then distilled for 2 hours under normal pressure at constant temperature and 465 ml of aqueous hydrobromic acid and water, the reaction by-product, was removed. The residue was dissolved in 550 ml of acetone, and 500 ml of ethyl acetate and 670 ml of ether were added thereto. The reaction solution was stirred for 30 minutes, cooled to 0° C. and then allowed to stand for 3 hours. The resulting solid product was filtered, washed with 400 ml of ethyl acetate and then dried to obtain 97 g of the first crop of the title compound. The filtrate was then concentrated. The residue was dissolved in 450 ml of acetone, diluted with 680 ml of ether and then allowed to stand at 0° C. for 12 hours. The resulting solid product was filtered, collected, and washed with 450 ml of ethyl acetate to obtain 32.5 g of the second crop of the title compound. the resulting suspension was reacted at 126° C. for 30 minutes under refluxing The reaction solution was then distilled for 2 hours under normal pressure at constant temperature and 465 ml of aqueous hydrobromic acid and water the reaction by-product, was removed The residue was dissolved in 550 ml of acetone 500 ml of ethyl acetate and 670 ml of ether were added to stand for 3 hours The resulting solid product was filtered washed with 400 ml of ethyl acetate dried