ethyl (3S)-4-azido-3-hydroxybutanoate

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

実験手順: To a mixture of ethyl (S)-4-chloro-3-hydroxybutyrate (1 93 g, 1.16 mol, optical purity:98.5% ee) and N,N-dimethylformamide (1.4 Lit.) is added sodium azide (151 g, 2.32 mol) and the mixture was stirred at 100°-110° C. for 2 hours. After cooling N,N-dimethylformamide was distilled off and to the residue was added water (1 Lit.). The mixture was extracted with ethyl acetate and the extract was dried over magnesium sulfate. By distillation off ethyl acetate under vacuo, there is obtained ethyl (S)-4-azido-3-hydroxybutyrate as a crude product (206 g). Then the crude product was dissolved in methanol (1 Lit.) and to it 5% palladium-carbon (10 g) was added. The mixture was stirred for 17 hours at room temperature under a hydrogen atmosphere. After the reaction was over, palladium-carbon was filtered off and the solvent was distilled off under vacuo. The resulting product was recrystallized from acetone-water to give (S)-4-hydroxy-2-pyrrolidone (99 g, 0.98 mol, yield:84%) as a colorless crystalline solid. Optical purity:98.3% ee, Specific rotation:[α]D22 -57.6°(c=1.00, H2O). was distilled off and to the residue was added water (1 Lit.) The mixture was extracted with ethyl acetate the extract was dried over magnesium sulfate By distillation off ethyl acetate under vacuo

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

実験手順: To a mixture of ethyl (S)-4-chloro-3-hydroxybutyrate (1 93 g, 1.16 mol, optical purity:98.5% ee) and N,N-dimethylformamide (1.4 Lit.) is added sodium azide (151 g, 2.32 mol) and the mixture was stirred at 100°-110° C. for 2 hours. After cooling N,N-dimethylformamide was distilled off and to the residue was added water (1 Lit.). The mixture was extracted with ethyl acetate and the extract was dried over magnesium sulfate. By distillation off ethyl acetate under vacuo, there is obtained ethyl (S)-4-azido-3-hydroxybutyrate as a crude product (206 g). Then the crude product was dissolved in methanol (1 Lit.) and to it 5% palladium-carbon (10 g) was added. The mixture was stirred for 17 hours at room temperature under a hydrogen atmosphere. After the reaction was over, palladium-carbon was filtered off and the solvent was distilled off under vacuo. The resulting product was recrystallized from acetone-water to give (S)-4-hydroxy-2-pyrrolidone (99 g, 0.98 mol, yield:84%) as a colorless crystalline solid. Optical purity:98.3% ee, Specific rotation:[α]D22 -57.6°(c=1.00, H2O). was distilled off and to the residue was added water (1 Lit.) The mixture was extracted with ethyl acetate the extract was dried over magnesium sulfate By distillation off ethyl acetate under vacuo

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

実験手順: To a mixture of ethyl (S)-4-chloro-3-hydroxybutyrate (1 93 g, 1.16 mol, optical purity:98.5% ee) and N,N-dimethylformamide (1.4 Lit.) is added sodium azide (151 g, 2.32 mol) and the mixture was stirred at 100°-110° C. for 2 hours. After cooling N,N-dimethylformamide was distilled off and to the residue was added water (1 Lit.). The mixture was extracted with ethyl acetate and the extract was dried over magnesium sulfate. By distillation off ethyl acetate under vacuo, there is obtained ethyl (S)-4-azido-3-hydroxybutyrate as a crude product (206 g). Then the crude product was dissolved in methanol (1 Lit.) and to it 5% palladium-carbon (10 g) was added. The mixture was stirred for 17 hours at room temperature under a hydrogen atmosphere. After the reaction was over, palladium-carbon was filtered off and the solvent was distilled off under vacuo. The resulting product was recrystallized from acetone-water to give (S)-4-hydroxy-2-pyrrolidone (99 g, 0.98 mol, yield:84%) as a colorless crystalline solid. Optical purity:98.3% ee, Specific rotation:[α]D22 -57.6°(c=1.00, H2O). was distilled off and to the residue was added water (1 Lit.) The mixture was extracted with ethyl acetate the extract was dried over magnesium sulfate By distillation off ethyl acetate under vacuo

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

実験手順: Instead of ethyl 3-hydroxybutyrate used in Example 1, ethyl 4-azido-3-hydroxybutyrate was used. The reaction was carried out for 1 hour and ethyl (S)-4-azido-3-hydroxybutyrate (80.2% e.e) was obtained at 83.5% conversion.

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

実験手順: To a mixture of ethyl (S)-4-chloro-3-hydroxybutyrate (1 93 g, 1.16 mol, optical purity:98.5% ee) and N,N-dimethylformamide (1.4 Lit.) is added sodium azide (151 g, 2.32 mol) and the mixture was stirred at 100°-110° C. for 2 hours. After cooling N,N-dimethylformamide was distilled off and to the residue was added water (1 Lit.). The mixture was extracted with ethyl acetate and the extract was dried over magnesium sulfate. By distillation off ethyl acetate under vacuo, there is obtained ethyl (S)-4-azido-3-hydroxybutyrate as a crude product (206 g). Then the crude product was dissolved in methanol (1 Lit.) and to it 5% palladium-carbon (10 g) was added. The mixture was stirred for 17 hours at room temperature under a hydrogen atmosphere. After the reaction was over, palladium-carbon was filtered off and the solvent was distilled off under vacuo. The resulting product was recrystallized from acetone-water to give (S)-4-hydroxy-2-pyrrolidone (99 g, 0.98 mol, yield:84%) as a colorless crystalline solid. Optical purity:98.3% ee, Specific rotation:[α]D22 -57.6°(c=1.00, H2O). was distilled off and to the residue was added water (1 Lit.) The mixture was extracted with ethyl acetate the extract was dried over magnesium sulfate By distillation off ethyl acetate under vacuo