N-CBZ-(S)-(-)-2-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: Subsequently, to a solution of [(1S)-1-(hydroxymethyl)propyl]carbamic acid benzyl ester (4.27 g, 19.1 mmol) in dimethylformamide (128 ml) were added t-butyldiphenylsilyl chloride (5.97 ml, 22.9 mmol) and imidazole (1.56 g, 22.9 mmol) in an ice bath. The mixture was stirred at room temperature overnight. After checking the completion of the reaction, the reaction mixture was partitioned between ethyl acetate and 10% aqueous sodium chloride solution. The organic layer was washed successively with saturated aqueous sodium hydrogencarbonate solution and saturated aqueous sodium chloride solution, dried over anhydrous sodium sulfate, filtered and concentrated under reduced pressure. The residue was purified by chromatography on a silica gel column using n-hexane:ethyl acetate (6:1→4:1) as the eluant to afford [(1S)-1-(t-butyldiphenylsilyloxymethyl)propyl]carbamic acid benzyl ester (9.48 g, yield 100%) as a white solid. the completion of the reaction the reaction mixture was partitioned between ethyl acetate and 10% aqueous sodium chloride solution The organic layer was washed successively with saturated aqueous sodium hydrogencarbonate solution and saturated aqueous sodium chloride solution dried over anhydrous sodium sulfate filtered concentrated under reduced pressure The residue was purified by chromatography on a silica gel column

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

实验步骤: Subsequently, to a solution of [(1S)-1-(hydroxymethyl)propyl]carbamic acid benzyl ester (4.27 g, 19.1 mmol) in dimethylformamide (128 ml) were added t-butyldiphenylsilyl chloride (5.97 ml, 22.9 mmol) and imidazole (1.56 g, 22.9 mmol) in an ice bath. The mixture was stirred at room temperature overnight. After checking the completion of the reaction, the reaction mixture was partitioned between ethyl acetate and 10% aqueous sodium chloride solution. The organic layer was washed successively with saturated aqueous sodium hydrogencarbonate solution and saturated aqueous sodium chloride solution, dried over anhydrous sodium sulfate, filtered and concentrated under reduced pressure. The residue was purified by chromatography on a silica gel column using n-hexane:ethyl acetate (6:1→4:1) as the eluant to afford [(1S)-1-(t-butyldiphenylsilyloxymethyl)propyl]carbamic acid benzyl ester (9.48 g, yield 100%) as a white solid. the completion of the reaction the reaction mixture was partitioned between ethyl acetate and 10% aqueous sodium chloride solution The organic layer was washed successively with saturated aqueous sodium hydrogencarbonate solution and saturated aqueous sodium chloride solution dried over anhydrous sodium sulfate filtered concentrated under reduced pressure The residue was purified by chromatography on a silica gel column

反应条件: temp:0.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

实验步骤: To a cold (0° C.) solution of (S)-2-amino-1-butanol (2.0 g, 22.5 mmol) in acetone/H2O 1:1 (50 mL), Na2CO3 (8.7 g, 81.9 mmol) and BnOCOCl (5.8 g, 33.8 mmol) were added. After stirring at 0° C. for 1 h, the solid was filtered off and washed with acetone (2×30 mL). The filtrates were concentrated in vacuo and the residue was purified by column chromatography on silica (100% CH2Cl2 to CH2Cl2/MeOH 20:1) to obtain alcohol 7 as a white solid (2.14 g, 43% yield). the solid was filtered off washed with acetone (2×30 mL) The filtrates were concentrated in vacuo the residue was purified by column chromatography on silica (100% CH2Cl2 to CH2Cl2/MeOH 20:1)

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

实验步骤: A solution of benzyl [(1S)-1-(hydroxymethyl)propyl]carbamate (30.0 g) in dimethyl sulfoxide (260 mL) was ice-cooled under a nitrogen atmosphere, and triethylamine (56.9 mL) and a solution of sulfur trioxide pyridine complex (71.3 g) in dimethyl sulfoxide (260 mL) was successively added. The mixture was stirred at the same temperature for 1 hr, and at room temperature for 4 hr. A 1 mol/L aqueous citric acid solution (450 mL) was added to the reaction solution, and the mixture was extracted with diethyl ether. The obtained organic layer was washed with saturated brine, dried over anhydrous magnesium sulfate, and concentrated under reduced pressure. The residue was purified by silica gel column chromatography (eluent: ethyl acetate/hexane=0→30%) to give the title compound as a colorless oil (yield: 16.3 g, 55%). cooled under a nitrogen atmosphere at room temperature for 4 hr the mixture was extracted with diethyl ether The obtained organic layer was washed with saturated brine dried over anhydrous magnesium sulfate concentrated under reduced pressure The residue was purified by silica gel column chromatography (eluent: ethyl acetate/hexane=0→30%)

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

实验步骤: A solution of benzyl[(1S)-1-(hydroxymethyl)propyl]carbamate (30.0 g) in dimethyl sulfoxide (260 mL) was ice-cooled under a nitrogen atmosphere, and triethylamine (56.9 mL) and a solution of sulfur trioxide•pyridine complex (71.3 g) in dimethyl sulfoxide (260 mL) was successively added. The mixture was stirred at the same temperature for 1 hr, and at room temperature for 4 hr. A 1 mol/L aqueous citric acid solution (450 mL) was added to the reaction solution, and the mixture was extracted with diethyl ether. The obtained organic layer was washed with saturated brine, dried over anhydrous magnesium sulfate, and concentrated under reduced pressure. The residue was purified by silica gel column chromatography (eluent: ethyl acetate/hexane=0→30%) to give the title compound as a colorless oil (yield: 16.3 g, 55%). cooled under a nitrogen atmosphere at room temperature for 4 hr the mixture was extracted with diethyl ether The obtained organic layer was washed with saturated brine dried over anhydrous magnesium sulfate concentrated under reduced pressure The residue was purified by silica gel column chromatography (eluent: ethyl acetate/hexane=0→30%)

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

实验步骤: Subsequently, to a solution of [(1S)-1-(hydroxymethyl)propyl]carbamic acid benzyl ester (4.27 g, 19.1 mmol) in dimethylformamide (128 ml) were added t-butyldiphenylsilyl chloride (5.97 ml, 22.9 mmol) and imidazole (1.56 g, 22.9 mmol) in an ice bath. The mixture was stirred at room temperature overnight. After checking the completion of the reaction, the reaction mixture was partitioned between ethyl acetate and 10% aqueous sodium chloride solution. The organic layer was washed successively with saturated aqueous sodium hydrogencarbonate solution and saturated aqueous sodium chloride solution, dried over anhydrous sodium sulfate, filtered and concentrated under reduced pressure. The residue was purified by chromatography on a silica gel column using n-hexane:ethyl acetate (6:1→4:1) as the eluant to afford [(1S)-1-(t-butyldiphenylsilyloxymethyl)propyl]carbamic acid benzyl ester (9.48 g, yield 100%) as a white solid. the completion of the reaction the reaction mixture was partitioned between ethyl acetate and 10% aqueous sodium chloride solution The organic layer was washed successively with saturated aqueous sodium hydrogencarbonate solution and saturated aqueous sodium chloride solution dried over anhydrous sodium sulfate filtered concentrated under reduced pressure The residue was purified by chromatography on a silica gel column

反应条件: temp:0.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

实验步骤: To a cold (0° C.) solution of (S)-2-amino-1-butanol (2.0 g, 22.5 mmol) in acetone/H2O 1:1 (50 mL), Na2CO3 (8.7 g, 81.9 mmol) and BnOCOCl (5.8 g, 33.8 mmol) were added. After stirring at 0° C. for 1 h, the solid was filtered off and washed with acetone (2×30 mL). The filtrates were concentrated in vacuo and the residue was purified by column chromatography on silica (100% CH2Cl2 to CH2Cl2/MeOH 20:1) to obtain alcohol 7 as a white solid (2.14 g, 43% yield). the solid was filtered off washed with acetone (2×30 mL) The filtrates were concentrated in vacuo the residue was purified by column chromatography on silica (100% CH2Cl2 to CH2Cl2/MeOH 20:1)