N-Benzyl-3-aminopropan-1-ol

反応条件: temp:0.00; pressure:0.00; stir:

反応条件: temp:0.00; pressure:0.00; stir:

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

実験手順: A solution of 3-benzylamino-propan-1-ol (14 g, 88.0 mmol) and epichlorohydrin (81.4 g, 880 mmol) was heated to 40° C. After stirring for 3 h the reaction was cooled and excess epichlorohydrin was removed by evaporation in vacuo. Sulfuric acid (10 mL) was added slowly, then the reaction flask was placed in a preheated oil bath at 150° C. Stirring proceeded for 1 h, then the reaction was allowed to cool to room temperature and quenched with the addition of ice. The mixture was adjusted to a basic pH with 10% aqueous Na2CO3 solution and extracted with EtOAc (3×300 mL). The combined organic layers were dried over anhydrous MgSO4, filtered, and dried under reduced pressure. The resulting residue was purified by flash chromatography (70:28:2 hexanes/CH2Cl2/2M NH4OH aq) to afford 5 g of a light yellow oil. was cooled excess epichlorohydrin was removed by evaporation in vacuo Sulfuric acid (10 mL) was added slowly the reaction flask was placed in a preheated oil bath at 150° C Stirring proceeded for 1 h quenched with the addition of ice extracted with EtOAc (3×300 mL) The combined organic layers were dried over anhydrous MgSO4 filtered dried under reduced pressure The resulting residue was purified by flash chromatography (70:28:2 hexanes/CH2Cl2/2M NH4OH aq)

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

実験手順: To a solution of benzaldehyde (10 g, 94.23 mmol) and trimethylorthoformate (15.5 mL, 141 mmol ) in MeOH (300 mL) was added dropwise 3-amino-1-propanol (7.21 mL, 94.23 mmol) at room temperature. The reaction was allowed to stir at room temperature for 5 hours followed by cooling to 0° C. in an ice bath. Sodium borohydride (3.56 g, 94.23 mmol) was added in two portions and when the bubbling stopped the solvent was evaporated. The resulting residue was partitioned between ethyl acetate (75 mL) and water (75 mL). The aqueous layer was extracted twice with ethyl acetate (75 mL). The ethyl acetate extracts were collected and washed twice with Brine (50 mL), dried over MgSO4, filtered, and concentrated. Drying afforded 14.42 g (93%) of the compound which was used in the next step of synthesis without further purification. by cooling to 0° C. in an ice bath was evaporated The resulting residue was partitioned between ethyl acetate (75 mL) and water (75 mL) The aqueous layer was extracted twice with ethyl acetate (75 mL) The ethyl acetate extracts were collected washed twice with Brine (50 mL) dried over MgSO4 filtered concentrated Drying

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

実験手順: A solution of 11.48 g (64,1 mmol) of 4,5-dichloro-2-methyl-3(2H)-pyridazinone and 31.84 g (193.0 mmol) of 3-(N-benzylamino)propanol in 250 ml of water is boiled for 25 hours while stirring. The mixture is cooled, its pH is set with concentrated hydrochloric acid to 3 and it is extracted with 2×400 ml of ethyl acetate. The organic phase is dried and evaporated, 10 ml of ethyl acetate are added to the evaporation residue, then it is left to stand overnight at −10° C. The precipitated crystals are filtered and washed with ethyl acetate and then with diethyl ether. In this way 10.60 g (54%) of the title compound are obtained with a melting point of 94-95° C. The mixture is cooled is extracted with 2×400 ml of ethyl acetate The organic phase is dried evaporated 10 ml of ethyl acetate are added to the evaporation residue it is left The precipitated crystals are filtered washed with ethyl acetate

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

実験手順: A solution of 3-aminopropan-1-ol (3 g, 39.9 mmol) and benzaldehyde (4.05 mL, 39.9 mmol) in methanol (200 mL) was stirred at room temperature overnight. The solution was cooled to 0° C., and sodium borohydride (1.813 g, 47.9 mmol) was added slowly in several portions. The resulting mixture was stirred at room temperature for three hours, and then it was partitioned between water and dichloromethane (3x). The organic extracts were combined and dried over Na2SO4, the drying agent was removed by filtration, and the solution was concentrated in vacuo to give the title compound as an oil (6.5 g, 98%). it was partitioned between water and dichloromethane (3x) dried over Na2SO4 the drying agent was removed by filtration the solution was concentrated in vacuo

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

実験手順: 3-amino-1-propanol (150 g) was dissolved in tetrahydrofuran (200 mL), followed by the addition of benzylamine(23.8 g). The mixture was stirred at room temperature for 1 hour. Subsequently, the reaction mixture was diluted with ethyl acetate, was sequentially washed with water and a saturated aqueous solution of sodium chloride, and was then dried over anhydrous sodium sulfate. The solvent was removed to obtain 3-(benzylamino)-1-propanol (20.1 g, 61%). was sequentially washed with water a saturated aqueous solution of sodium chloride, and was then dried over anhydrous sodium sulfate The solvent was removed

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

実験手順: 3-amino-1-propanol (150 g) was dissolved in tetrahydrofuran (200 mL), followed by the addition of benzylamine(23.8 g). The mixture was stirred at room temperature for 1 hour. Subsequently, the reaction mixture was diluted with ethyl acetate, was sequentially washed with water and a saturated aqueous solution of sodium chloride, and was then dried over anhydrous sodium sulfate. The solvent was removed to obtain 3-(benzylamino)-1-propanol (20.1 g, 61%). was sequentially washed with water a saturated aqueous solution of sodium chloride, and was then dried over anhydrous sodium sulfate The solvent was removed

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

実験手順: A solution of 3-aminopropan-1-ol (3 g, 39.9 mmol) and benzaldehyde (4.05 mL, 39.9 mmol) in methanol (200 mL) was stirred at room temperature overnight. The solution was cooled to 0° C., and sodium borohydride (1.813 g, 47.9 mmol) was added slowly in several portions. The resulting mixture was stirred at room temperature for three hours, and then it was partitioned between water and dichloromethane (3×). The organic extracts were combined and dried over Na2SO4, the drying agent was removed by filtration, and the solution was concentrated in vacuo to give the title compound as an oil (6.5 g, 98%). it was partitioned between water and dichloromethane (3×) dried over Na2SO4 the drying agent was removed by filtration the solution was concentrated in vacuo

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

実験手順: To a solution of benzaldehyde (10 g, 94.23 mmol) and trimethylorthoformate (15.5 mL, 141 mmol ) in MeOH (300 mL) was added dropwise 3-amino-1-propanol (7.21 mL, 94.23 mmol) at room temperature. The reaction was allowed to stir at room temperature for 5 hours followed by cooling to 0° C. in an ice bath. Sodium borohydride (3.56 g, 94.23 mmol) was added in two portions and when the bubbling stopped the solvent was evaporated. The resulting residue was partitioned between ethyl acetate (75 mL) and water (75 mL). The aqueous layer was extracted twice with ethyl acetate (75 mL). The ethyl acetate extracts were collected and washed twice with Brine (50 mL), dried over MgSO4, filtered, and concentrated. Drying afforded 14.42 g (93%) of the compound which was used in the next step of synthesis without further purification. by cooling to 0° C. in an ice bath was evaporated The resulting residue was partitioned between ethyl acetate (75 mL) and water (75 mL) The aqueous layer was extracted twice with ethyl acetate (75 mL) The ethyl acetate extracts were collected washed twice with Brine (50 mL) dried over MgSO4 filtered concentrated Drying

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

実験手順: A solution of 3-benzylamino-propan-1-ol (14 g, 88.0 mmol) and epichlorohydrin (81.4 g, 880 mmol) was heated to 40° C. After stirring for 3 h the reaction was cooled and excess epichlorohydrin was removed by evaporation in vacuo. Sulfuric acid (10 mL) was added slowly, then the reaction flask was placed in a preheated oil bath at 150° C. Stirring proceeded for 1 h, then the reaction was allowed to cool to room temperature and quenched with the addition of ice. The mixture was adjusted to a basic pH with 10% aqueous Na2CO3 solution and extracted with EtOAc (3×300 mL). The combined organic layers were dried over anhydrous MgSO4, filtered, and dried under reduced pressure. The resulting residue was purified by flash chromatography (70:28:2 hexanes/CH2Cl2/2M NH4OH aq) to afford 5 g of a light yellow oil. was cooled excess epichlorohydrin was removed by evaporation in vacuo Sulfuric acid (10 mL) was added slowly the reaction flask was placed in a preheated oil bath at 150° C Stirring proceeded for 1 h quenched with the addition of ice extracted with EtOAc (3×300 mL) The combined organic layers were dried over anhydrous MgSO4 filtered dried under reduced pressure The resulting residue was purified by flash chromatography (70:28:2 hexanes/CH2Cl2/2M NH4OH aq)

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

実験手順: To a solution of benzaldehyde (10 g, 94.23 mmol) and trimethylorthoformate (15.5 mL, 141 mmol ) in MeOH (300 mL) was added dropwise 3-amino-1-propanol (7.21 mL, 94.23 mmol) at room temperature. The reaction was allowed to stir at room temperature for 5 hours followed by cooling to 0° C. in an ice bath. Sodium borohydride (3.56 g, 94.23 mmol) was added in two portions and when the bubbling stopped the solvent was evaporated. The resulting residue was partitioned between ethyl acetate (75 mL) and water (75 mL). The aqueous layer was extracted twice with ethyl acetate (75 mL). The ethyl acetate extracts were collected and washed twice with Brine (50 mL), dried over MgSO4, filtered, and concentrated. Drying afforded 14.42 g (93%) of the compound which was used in the next step of synthesis without further purification. by cooling to 0° C. in an ice bath was evaporated The resulting residue was partitioned between ethyl acetate (75 mL) and water (75 mL) The aqueous layer was extracted twice with ethyl acetate (75 mL) The ethyl acetate extracts were collected washed twice with Brine (50 mL) dried over MgSO4 filtered concentrated Drying