tert-butyl N-(2-methylsulfanylethyl)carbamate

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: To a mixture of tert-butyl 2-(methylsulfanyl)ethylcarbamate (3.5 g) and tetrahydrofuran (20 mL) was added lithium aluminum hydride (1.39 g) with stirring under ice-cooling and the mixture was heated under reflux for 2 hrs. After cooling the reaction mixture, sodium sulfate 10 hydrate (5 g) was added, and the solid was filtered off. The filtrate was concentrated and diluted with tetrahydrofuran, and di-tert-butyl dicarbonate was added dropwise with stirring under ice-cooling. After stirring at room temperature for 30 min, the reaction mixture was concentrated, diluted with ethyl acetate and washed with water. The organic layer was dried over anhydrous magnesium sulfate and concentrated. The residue was subjected to silica gel column chromatography, and tert-butyl N-methyl-N-[2-(methylsulfanyl)ethyl]carbamate was obtained as a colorless oil (0.82 g, yield 22%) from a fraction eluted with ethyl acetate-hexane (1:4, volume ratio). cooling the mixture was heated under reflux for 2 hrs was added the solid was filtered off The filtrate was concentrated diluted with tetrahydrofuran, and di-tert-butyl dicarbonate was added dropwise with stirring under ice- cooling After stirring at room temperature for 30 min the reaction mixture was concentrated diluted with ethyl acetate washed with water The organic layer was dried over anhydrous magnesium sulfate concentrated

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: To a mixture of tert-butyl 2-(methylsulfanyl)ethylcarbamate (3.5 g) and tetrahydrofuran (20 mL) was added lithium aluminum hydride (1.39 g) with stirring under ice-cooling and the mixture was heated under reflux for 2 hrs. After cooling the reaction mixture, sodium sulfate 10 hydrate (5 g) was added, and the solid was filtered off. The filtrate was concentrated and diluted with tetrahydrofuran, and di-tert-butyl dicarbonate was added dropwise with stirring under ice-cooling. After stirring at room temperature for 30 min, the reaction mixture was concentrated, diluted with ethyl acetate and washed with water. The organic layer was dried over anhydrous magnesium sulfate and concentrated. The residue was subjected to silica gel column chromatography, and tert-butyl N-methyl-N-[2-(methylsulfanyl)ethyl]carbamate was obtained as a colorless oil (0.82 g, yield 22%) from a fraction eluted with ethyl acetate-hexane (1:4, volume ratio). cooling the mixture was heated under reflux for 2 hrs was added the solid was filtered off The filtrate was concentrated diluted with tetrahydrofuran, and di-tert-butyl dicarbonate was added dropwise with stirring under ice- cooling After stirring at room temperature for 30 min the reaction mixture was concentrated diluted with ethyl acetate washed with water The organic layer was dried over anhydrous magnesium sulfate concentrated

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

実験手順: In a dried reaction flask, the crude tert-butyl 2-(methylthio)ethylcarbamate (2.464 g, about 11.0 mmol) was dissolved in tetrahydrofuran (22 mL). To the mixture was added 77% mCPBA (5.698 g, 25.42 mmol) in portion at 0° C. The mixture was stirred for 1 hr. Water, saturated aqueous sodium bicarbonate solution and ethyl acetate were added. The mixture was extracted with ethyl acetate. The combined organic phase was washed with saturated salt water, dried over anhydrous sodium sulfate, and was purified by silica gel column chromatography with ethyl acetate to obtain a white solid (0.95 g) in 38.7% yield. In a dried reaction flask The mixture was extracted with ethyl acetate The combined organic phase was washed with saturated salt water dried over anhydrous sodium sulfate was purified by silica gel column chromatography with ethyl acetate

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

実験手順: In a dried reaction flask, 2-(methylthio)ethylamine hydrochloride (6.382 g, 50.0 mmol) and TEA (triethylamine) (13.9 mL, 100 mmol) were dissolved in tetrahydrofuran (63.3 mL). To the mixture was added dropwise Boc2O(di-tert-butyl dicarbonate) (12.3 g, 56.4 mmol) dissolved in tetrahydrofuran (10 mL) under an ice-salt bath. The mixture was stirred at room temperature for 21 hr. Water and ethyl acetate were added. The mixture was extracted with ethyl acetate. The combined organic phase was washed with brine, dried over anhydrous sodium sulfate, and concentrated to produce a crude colorless oil (11.752 g). The mixture was extracted with ethyl acetate The combined organic phase was washed with brine dried over anhydrous sodium sulfate concentrated

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

実験手順: To a mixture of tert-butyl 2-(methylsulfanyl)ethylcarbamate (3.5 g) and tetrahydrofuran (20 mL) was added lithium aluminum hydride (1.39 g) with stirring under ice-cooling and the mixture was heated under reflux for 2 hrs. After cooling the reaction mixture, sodium sulfate 10 hydrate (5 g) was added, and the solid was filtered off. The filtrate was concentrated and diluted with tetrahydrofuran, and di-tert-butyl dicarbonate was added dropwise with stirring under ice-cooling. After stirring at room temperature for 30 min, the reaction mixture was concentrated, diluted with ethyl acetate and washed with water. The organic layer was dried over anhydrous magnesium sulfate and concentrated. The residue was subjected to silica gel column chromatography, and tert-butyl N-methyl-N-[2-(methylsulfanyl)ethyl]carbamate was obtained as a colorless oil (0.82 g, yield 22%) from a fraction eluted with ethyl acetate-hexane (1:4, volume ratio). cooling the mixture was heated under reflux for 2 hrs was added the solid was filtered off The filtrate was concentrated diluted with tetrahydrofuran, and di-tert-butyl dicarbonate was added dropwise with stirring under ice- cooling After stirring at room temperature for 30 min the reaction mixture was concentrated diluted with ethyl acetate washed with water The organic layer was dried over anhydrous magnesium sulfate concentrated