(R)-(-)-2-苄氨基-1-丁醇

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

实验步骤: Sodium triacetoxyborohydride (4.63 g) was added portionwisely to a mixture of (R)-(-)-2-amino-1-butanol (1.5 g) and benzaldehyde (1.79 g) in dichloromethane (50 ml) at 0° C. and the whole was stirred at room temperature overnight. The mixture was washed with sodium carbonate solution and brine, dried over sodium sulfate, and evaporated in vacuo to give (R)-2-benzylamino-1-butanol (2.69 g) [IR (Neat): 3292, 1460, 1350, 1136, 1061 cm−1]. A solution of chloroacetyl chloride (2.1 g) in tetrahydrofuran (4 ml) was added to a mixture of the obtained oil (2.69 g) and potassium carbonate (4.6 g) in a mixture of acetone (20 ml) and water (20 ml) at 0° C. After 1 hour of stirring, the solvent was replaced with ethyl acetate. The organic layer was separated, washed with brine, dried over sodium sulfate, and evaporated in vacuo. The residue was purified by column chromatography on silica gel to give N-benzyl-N-[(2R)-2-(1-hydroxybutyl)]-2-chloroacet amide (2.73 g) [IR (Neat): 3430, 1640, 1450, 1420, 1355, 1045 cm−1, MASS (APCI): 256 (M+H)+, 220] as an oil. Potassium tert-butoxide (1.22 g) was added to a solution of the above obtained oil (2.7 g) in tert-butanol (20 ml) portionwisely at room temperature and the whole was stirred overnight. The mixture was evaporated in vacuo, and ethyl acetate and water were added to the residue. The organic layer was separated, washed with brine, dried over sodium sulfate, and evaporated in vacuo to give (5R)-4-benzyl-5ethyl-3-morpholinone (2.33 g) as an oil. The mixture was washed with sodium carbonate solution and brine dried over sodium sulfate evaporated in vacuo

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

实验步骤: Sodium triacetoxyborohydride (4.63 g) was added portionwisely to a mixture of (R)-(-)-2-amino-1-butanol (1.5 g) and benzaldehyde (1.79 g) in dichloromethane (50 ml) at 0° C. and the whole was stirred at room temperature overnight. The mixture was washed with sodium carbonate solution and brine, dried over sodium sulfate, and evaporated in vacuo to give (R)-2-benzylamino-1-butanol (2.69 g) [IR (Neat): 3292, 1460, 1350, 1136, 1061 cm−1]. A solution of chloroacetyl chloride (2.1 g) in tetrahydrofuran (4 ml) was added to a mixture of the obtained oil (2.69 g) and potassium carbonate (4.6 g) in a mixture of acetone (20 ml) and water (20 ml) at 0° C. After 1 hour of stirring, the solvent was replaced with ethyl acetate. The organic layer was separated, washed with brine, dried over sodium sulfate, and evaporated in vacuo. The residue was purified by column chromatography on silica gel to give N-benzyl-N-[(2R)-2-(1-hydroxybutyl)]-2-chloroacet amide (2.73 g) [IR (Neat): 3430, 1640, 1450, 1420, 1355, 1045 cm−1, MASS (APCI): 256 (M+H)+, 220] as an oil. Potassium tert-butoxide (1.22 g) was added to a solution of the above obtained oil (2.7 g) in tert-butanol (20 ml) portionwisely at room temperature and the whole was stirred overnight. The mixture was evaporated in vacuo, and ethyl acetate and water were added to the residue. The organic layer was separated, washed with brine, dried over sodium sulfate, and evaporated in vacuo to give (5R)-4-benzyl-5ethyl-3-morpholinone (2.33 g) as an oil. The mixture was washed with sodium carbonate solution and brine dried over sodium sulfate evaporated in vacuo

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

实验步骤: To a solution of (2R)-2-[(phenylmethyl)amino]-1-butanol (10.06 g, 56.1 mmol) in 1,2-dichloroethane (DCE) (250 mL) was added (R)-(−)-epichlorohydrin (6.75 g, 72.9 mmol) followed by lithium perchlorate (5.97 g, 56.1 mmol) under nitrogen. The reaction was stirred for 2 days at room temperature, then sodium ethoxide (52.4 mL, 140 mmol) was added and the reaction continued to stir for 3 days. Saturated NH4Cl was added, and the product was extracted with EtOAc. The organic layers were combined, dried over Na2SO4, and concentrated to afford the title compound (16.2 g) as a colorless oil. LC-MS (ES) m/z=236 [M+H]+. to stir for 3 days the product was extracted with EtOAc dried over Na2SO4 concentrated

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

实验步骤: To a solution of (2R)-2-[(phenylmethyl)amino]-1-butanol (10.06 g, 56.1 mmol) in 1,2-dichloroethane (DCE) (250 mL) was added (R)-(−)-epichlorohydrin (6.75 g, 72.9 mmol) followed by lithium perchlorate (5.97 g, 56.1 mmol) under nitrogen. The reaction was stirred for 2 days at room temperature, then sodium ethoxide (52.4 mL, 140 mmol) was added and the reaction continued to stir for 3 days. Saturated NH4Cl was added, and the product was extracted with EtOAc. The organic layers were combined, dried over Na2SO4, and concentrated to afford the title compound (16.2 g) as a colorless oil. LC-MS (ES) m/z=236 [M+H]+. to stir for 3 days the product was extracted with EtOAc dried over Na2SO4 concentrated

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

实验步骤: To a solution of (2R)-2-[(phenylmethyl)amino]-1-butanol (10.06 g, 56.1 mmol) in 1,2-dichloroethane (DCE) (250 mL) was added (R)-(−)-epichlorohydrin (6.75 g, 72.9 mmol) followed by lithium perchlorate (5.97 g, 56.1 mmol) under nitrogen. The reaction was stirred for 2 days at room temperature, then sodium ethoxide (52.4 mL, 140 mmol) was added and the reaction continued to stir for 3 days. Saturated NH4Cl was added, and the product was extracted with EtOAc. The organic layers were combined, dried over Na2SO4, and concentrated to afford the title compound (16.2 g) as a colorless oil. LC-MS (ES) m/z=236 [M+H]+. to stir for 3 days the product was extracted with EtOAc dried over Na2SO4 concentrated

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

实验步骤: To (R)-(−)-2-amino-1-butanol (5 g, 56.1 mmol) in CH3OH (120 mL) was added benzaldehyde (6.24 mL, 61.7 mmol), and the reaction mixture was stirred under nitrogen for 15 minutes. The mixture was then cooled in an ice bath and sodium borohydride (2.33 g, 61.7 mmol) was added portionwise. The mixture was stirred in the ice bath for 1.5 hours. NaOH (6 N, 25 mL) was added and the mixture was concentrated. The resulting residue was taken up in 100 mL H2O and extracted with Et2O (2×). The organics were combined, dried over Na2SO4 and concentrated to afford the title compound (10.92 g) as a fluffy white solid. LC-MS (ES) m/z=180 [M+H]+. The mixture was then cooled in an ice bath the mixture was concentrated extracted with Et2O (2×) dried over Na2SO4 concentrated

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

实验步骤: To (R)-(−)-2-amino-1-butanol (5 g, 56.1 mmol) in CH3OH (120 mL) was added benzaldehyde (6.24 mL, 61.7 mmol), and the reaction mixture was stirred under nitrogen for 15 minutes. The mixture was then cooled in an ice bath and sodium borohydride (2.33 g, 61.7 mmol) was added portionwise. The mixture was stirred in the ice bath for 1.5 hours. NaOH (6 N, 25 mL) was added and the mixture was concentrated. The resulting residue was taken up in 100 mL H2O and extracted with Et2O (2×). The organics were combined, dried over Na2SO4 and concentrated to afford the title compound (10.92 g) as a fluffy white solid. LC-MS (ES) m/z=180 [M+H]+. The mixture was then cooled in an ice bath the mixture was concentrated extracted with Et2O (2×) dried over Na2SO4 concentrated

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

实验步骤: Sodium triacetoxyborohydride (4.63 g) was added portionwisely to a mixture of (R)-(-)-2-amino-1-butanol (1.5 g) and benzaldehyde (1.79 g) in dichloromethane (50 ml) at 0° C. and the whole was stirred at room temperature overnight. The mixture was washed with sodium carbonate solution and brine, dried over sodium sulfate, and evaporated in vacuo to give (R)-2-benzylamino-1-butanol (2.69 g) [IR (Neat): 3292, 1460, 1350, 1136, 1061 cm−1]. A solution of chloroacetyl chloride (2.1 g) in tetrahydrofuran (4 ml) was added to a mixture of the obtained oil (2.69 g) and potassium carbonate (4.6 g) in a mixture of acetone (20 ml) and water (20 ml) at 0° C. After 1 hour of stirring, the solvent was replaced with ethyl acetate. The organic layer was separated, washed with brine, dried over sodium sulfate, and evaporated in vacuo. The residue was purified by column chromatography on silica gel to give N-benzyl-N-[(2R)-2-(1-hydroxybutyl)]-2-chloroacet amide (2.73 g) [IR (Neat): 3430, 1640, 1450, 1420, 1355, 1045 cm−1, MASS (APCI): 256 (M+H)+, 220] as an oil. Potassium tert-butoxide (1.22 g) was added to a solution of the above obtained oil (2.7 g) in tert-butanol (20 ml) portionwisely at room temperature and the whole was stirred overnight. The mixture was evaporated in vacuo, and ethyl acetate and water were added to the residue. The organic layer was separated, washed with brine, dried over sodium sulfate, and evaporated in vacuo to give (5R)-4-benzyl-5ethyl-3-morpholinone (2.33 g) as an oil. The mixture was washed with sodium carbonate solution and brine dried over sodium sulfate evaporated in vacuo