tert-butyl N-[2-[(2,2,2-trifluoroacetyl)amino]ethyl]carbamate

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

実験手順: Dissolve N-(t-butyloxycarbonyl)-N'-(trifluoroacetyl)-ethylenediamine (500 mg, 1.95 mmol) in anhydrous dimethylformamide (10 mL), cool to 0° C. and treat with sodium hydride (56 mg, 1.85 mmol, 80% dispersion in mineral oil). Stir for 15 minutes and add allyl bromide (0.25 mL, 2.9 mmol). Stir for 2.5 hours, dilute with ethyl acetate (50 mL) and extract with water (25 mL). Separate the organic phase and wash with brine (2×20 mL). Extract the combined aqueous phases with ethyl acetate (2×5 mL), dry (Na2SO4) and evaporate the solvent in vacuo. Purify by chromatography (2:1 hexane/ethyl acetate to 3:2 hexane/ethyl acetate) to give N-(t-butyloxycarbonyl)-N'-(trifluoroacetyl)-N'-(allyl)ethylenediamine (562 mg, 100%). Stir for 2.5 hours extract with water (25 mL) Separate the organic phase wash with brine (2×20 mL) Extract the combined aqueous phases with ethyl acetate (2×5 mL) dry (Na2SO4) evaporate the solvent in vacuo Purify by chromatography (2:1 hexane/ethyl acetate to 3:2 hexane/ethyl acetate)

反応条件: temp:0.00; pressure:0.00; stir:

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

実験手順: Dissolve N-(t-butyloxycarbonyl)-N'-(trifluoroacetyl)-ethylenediamine (500 mg, 1.95 mmol) in anhydrous dimethylformamide (10 mL), cool to 0° C. and treat with sodium hydride (56 mg, 1.85 mmol, 80% dispersion in mineral oil). Stir for 15 minutes and add allyl bromide (0.25 mL, 2.9 mmol). Stir for 2.5 hours, dilute with ethyl acetate (50 mL) and extract with water (25 mL). Separate the organic phase and wash with brine (2×20 mL). Extract the combined aqueous phases with ethyl acetate (2×5 mL), dry (Na2SO4) and evaporate the solvent in vacuo. Purify by chromatography (2:1 hexane/ethyl acetate to 3:2 hexane/ethyl acetate) to give N-(t-butyloxycarbonyl)-N'-(trifluoroacetyl)-N'-(allyl)ethylenediamine (562 mg, 100%). Stir for 2.5 hours extract with water (25 mL) Separate the organic phase wash with brine (2×20 mL) Extract the combined aqueous phases with ethyl acetate (2×5 mL) dry (Na2SO4) evaporate the solvent in vacuo Purify by chromatography (2:1 hexane/ethyl acetate to 3:2 hexane/ethyl acetate)

反応条件: temp:0.00; pressure:0.00; stir:

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

実験手順: Dissolve N-(t-butyloxycarbonyl)-N'-(trifluoroacetyl)-ethylenediamine (500 mg, 1.95 mmol) in anhydrous dimethylformamide (10 mL), cool to 0° C. and treat with sodium hydride (56 mg, 1.85 mmol, 80% dispersion in mineral oil). Stir for 15 minutes and add allyl bromide (0.25 mL, 2.9 mmol). Stir for 2.5 hours, dilute with ethyl acetate (50 mL) and extract with water (25 mL). Separate the organic phase and wash with brine (2×20 mL). Extract the combined aqueous phases with ethyl acetate (2×5 mL), dry (Na2SO4) and evaporate the solvent in vacuo. Purify by chromatography (2:1 hexane/ethyl acetate to 3:2 hexane/ethyl acetate) to give N-(t-butyloxycarbonyl)-N'-(trifluoroacetyl)-N'-(allyl)ethylenediamine (562 mg, 100%). Stir for 2.5 hours extract with water (25 mL) Separate the organic phase wash with brine (2×20 mL) Extract the combined aqueous phases with ethyl acetate (2×5 mL) dry (Na2SO4) evaporate the solvent in vacuo Purify by chromatography (2:1 hexane/ethyl acetate to 3:2 hexane/ethyl acetate)

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

実験手順: Dissolve N-(t-butyloxycarbonyl)-N'-(trifluoroacetyl)-ethylenediamine (500 mg, 1.95 mmol) in anhydrous dimethylformamide (10 mL), cool to 0° C. and treat with sodium hydride (56 mg, 1.85 mmol, 80% dispersion in mineral oil). Stir for 15 minutes and add allyl bromide (0.25 mL, 2.9 mmol). Stir for 2.5 hours, dilute with ethyl acetate (50 mL) and extract with water (25 mL). Separate the organic phase and wash with brine (2×20 mL). Extract the combined aqueous phases with ethyl acetate (2×5 mL), dry (Na2SO4) and evaporate the solvent in vacuo. Purify by chromatography (2:1 hexane/ethyl acetate to 3:2 hexane/ethyl acetate) to give N-(t-butyloxycarbonyl)-N'-(trifluoroacetyl)-N'-(allyl)-ethylenediamine (562 mg, 100%). Stir for 2.5 hours extract with water (25 mL) Separate the organic phase wash with brine (2×20 mL) Extract the combined aqueous phases with ethyl acetate (2×5 mL) dry (Na2SO4) evaporate the solvent in vacuo Purify by chromatography (2:1 hexane/ethyl acetate to 3:2 hexane/ethyl acetate)

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

実験手順: Dissolve N-(t-butyloxycarbonyl)-N'-(trifluoroacetyl)ethylenediamine (500 mg, 1.95 mmol) in anhydrous dimethylformamide (10 mL), cool to 0° C. and treat with sodium hydride (56 mg, 1.85 mmol, 80% dispersion in mineral oil). Stir for 15 minutes and add allyl bromide (0.25 mL, 2.9 mmol). Stir for 2.5 hours, dilute with ethyl acetate (50 mL) and extract with water (25 mL). Separate the organic phase and wash with brine (2×20 mL). Extract the combined aqueous phases with ethyl acetate (2×5 mL), dry (Na2SO4) and evaporate the solvent in vacuo. Purify by chromatography (2:1 hexane/ethyl acetate to 3:2 hexane/ethyl acetate) to give N-(t-butyloxycarbonyl)-N'-(trifluoroacetyl)-N'-(allyl)ethylenediamine (562mg, 100%). Stir for 2.5 hours extract with water (25 mL) Separate the organic phase wash with brine (2×20 mL) Extract the combined aqueous phases with ethyl acetate (2×5 mL) dry (Na2SO4) evaporate the solvent in vacuo Purify by chromatography (2:1 hexane/ethyl acetate to 3:2 hexane/ethyl acetate)

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

実験手順: Dissolve N-(t-butyloxycarbonyl)-N'-(trifluoroacetyl)ethylenediamine (500 mg, 1.95 mmol) in anhydrous dimethylformamide (10 mL), cool to 0° C. and treat with sodium hydride (56 mg, 1.85 mmol, 80% dispersion in mineral oil). Stir for 15 minutes and add allyl bromide (0.25 mL, 2.9 mmol). Stir for 2.5 hours, dilute with ethyl acetate (50 mL) and extract with water (25 mL). Separate the organic phase and wash with brine (2×20 mL). Extract the combined aqueous phases with ethyl acetate (2×5 mL), dry (Na2SO4) and evaporate the solvent in vacuo. Purify by chromatography (2:1 hexane/ethyl acetate to 3:2 hexane/ethyl acetate) to give N-(t-butyloxycarbonyl)-N'-(trifluoroacetyl)-N'-(allyl)ethylenediamine (562mg, 100%). Stir for 2.5 hours extract with water (25 mL) Separate the organic phase wash with brine (2×20 mL) Extract the combined aqueous phases with ethyl acetate (2×5 mL) dry (Na2SO4) evaporate the solvent in vacuo Purify by chromatography (2:1 hexane/ethyl acetate to 3:2 hexane/ethyl acetate)

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

実験手順: Dissolve N-(t-butyloxycarbonyl)-N'-(trifluoroacetyl)ethylenediamine (500 mg, 1.95 mmol) in anhydrous dimethylformamide (10 mL), cool to 0° C. and treat with sodium hydride (56 mg, 1.85 mmol, 80% dispersion in mineral oil). Stir for 15 minutes and add allyl bromide (0.25 mL, 2.9 mmol). Stir for 2.5 hours, dilute with ethyl acetate (50 mL) and extract with water (25 mL). Separate the organic phase and wash with brine (2×20 mL). Extract the combined aqueous phases with ethyl acetate (2×5 mL), dry (Na2SO4) and evaporate the solvent in vacuo. Purify by chromatography (2:1 hexane/ethyl acetate to 3:2 hexane/ethyl acetate) to give N-(t-butyloxycarbonyl)-N'-(trifluoroacetyl)-N'-(allyl)ethylenediamine (562mg, 100%). Stir for 2.5 hours extract with water (25 mL) Separate the organic phase wash with brine (2×20 mL) Extract the combined aqueous phases with ethyl acetate (2×5 mL) dry (Na2SO4) evaporate the solvent in vacuo Purify by chromatography (2:1 hexane/ethyl acetate to 3:2 hexane/ethyl acetate)

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

実験手順: The compound (6.57 g, 25.6 mmol) obtained in step A was dissolved in tetrahydrofuran (100 ml), and the mixture was stirred under ice-cooling. Then, a suspension of lithium aluminum hydride (1.94 g, 51.2 mmol) in tetrahydrofuran (50 ml) was slowly added dropwise. Thereafter, the mixture was stood overnight at room temperature. The reaction mixture was ice-cooled again, water (2 ml), 1N aqueous sodium hydroxide solution (4 ml) and water (2 ml) were added in this order with stirring, and the mixture was stirred at room temperature for 5 hr. The insoluble material was filtered off through celite, and the obtained solution was concentrated under reduced pressure to give the title compound (4.56 g, yield 74%) as a yellow oil. cooling was slowly added dropwise cooled again with stirring the mixture was stirred at room temperature for 5 hr The insoluble material was filtered off through celite the obtained solution was concentrated under reduced pressure

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

実験手順: Dissolve N-(t-butyloxycarbonyl)-N'-(trifluoroacetyl)ethylenediamine (500 mg, 1.95 mmol) in anhydrous dimethylformamide (10 mL), cool to 0° C. and treat with sodium hydride (56 mg, 1.85 mmol, 80% dispersion in mineral oil). Stir for 15 minutes and add allyl bromide (0.25 mL, 2.9 mmol). Stir for 2.5 hours, dilute with ethyl acetate (50 mL) and extract with water (25 mL). Separate the organic phase and wash with brine (2×20 mL). Extract the combined aqueous phases with ethyl acetate (2×5 mL), dry (Na2SO4) and evaporate the solvent in vacuo. Purify by chromatography (2:1 hexane/ethyl acetate to 3:2 hexane/ethyl acetate) to give N-(t-butyloxycarbonyl)-N'-(trifluoroacetyl)-N'-(allyl)-ethylenediamine (562 mg, 100%). Stir for 2.5 hours extract with water (25 mL) Separate the organic phase wash with brine (2×20 mL) Extract the combined aqueous phases with ethyl acetate (2×5 mL) dry (Na2SO4) evaporate the solvent in vacuo Purify by chromatography (2:1 hexane/ethyl acetate to 3:2 hexane/ethyl acetate)