1-azido-3,3-dimethylbutan-2-one

反応条件: temp:0.00; pressure:0.00; stir:

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: A mixture of 1-bromopinacolone (0.5 mL, 3.7 mmol) and NaN3 (0.48 g, 7.38 mmol) in 50 mL acetone was stirred overnight at room temperature. It was then poured into brine and extracted with dichloromethane. The extracts were washed with brine, were dried over Na2SO4, filtered, and were evaporated to afford the title compound as a yellow oil (524 mg, 100%). 1H NMR (DMSO-d6) δ 4.39 (s, 2H), 1.10 (s, 9H); MS (DCI+) m/z 142 (M+H)+. extracted with dichloromethane The extracts were washed with brine were dried over Na2SO4 filtered were evaporated

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

実験手順: A mixture of 1-bromopinacolone (0.5 mL, 3.7 mmol) and NaN3 (0.48 g, 7.38 mmol) in 50 mL acetone was stirred overnight at room temperature. It was then poured into brine and extracted with dichloromethane. The extracts were washed with brine, were dried over Na2SO4, filtered, and were evaporated to afford the title compound as a yellow oil (524 mg, 100%). 1H NMR (DMSO-d6) δ 4.39 (s, 2H), 1.10 (s, 9H); MS (DCI+) m/z 142 (M+H)+. extracted with dichloromethane The extracts were washed with brine were dried over Na2SO4 filtered were evaporated

反応条件: temp:0.00; pressure:0.00; stir:

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 2 L three-necked round-bottom flask fitted with a mechanical stirrer were added azidopinacolone (28.6 g, 203 mmol, 1.0 equiv), methanol (1145 mL), concentrated HCl (18 mL), and 10% Pd/C (3.5 g, 50% water wet). The reaction mixture was stirred under hydrogen at 20 psi for 2 h, the mixture was filtered through a pad of Celite, and the residue rinsed with methanol (2×50 mL). The filtrate was concentrated under reduced pressure at a temperature below 40° C. The resulting wet solid was azeotroped with 2-propanol (2×100 mL), anhydrous ether (100 mL) was added, and the slurry which formed was stirred for 5 min. The solid product was collected by filtration, and the cake was washed with diethyl ether (2×30 mL) and then dried in vacuo to give aminopinacolone hydrochloride A-2. To a 2 L three-necked round-bottom flask fitted with a mechanical stirrer the mixture was filtered through a pad of Celite the residue rinsed with methanol (2×50 mL) The filtrate was concentrated under reduced pressure at a temperature below 40° C The resulting wet solid was azeotroped with 2-propanol (2×100 mL), anhydrous ether (100 mL) was added the slurry which formed was stirred for 5 min The solid product was collected by filtration the cake was washed with diethyl ether (2×30 mL) dried in vacuo

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

実験手順: To a 2 L three-necked round-bottom flask fitted with a mechanical stirrer was added bromopinacolone A-1 (134 g, 747 mmol, 1.0 equiv), acetone (1.2 L), and sodium azide (63.2 g, 971 mmol, 1.3 equiv). The reaction mixture was stirred at room-temperature overnight and then filtered, and the solids were washed with acetone (2×100 mL). The filtrate was concentrated in vacuo to provide azidopinacolone (105.0 g, 100%) as an oil. The crude material was used in the next step without further purification. To a 2 L three-necked round-bottom flask fitted with a mechanical stirrer filtered the solids were washed with acetone (2×100 mL) The filtrate was concentrated in vacuo

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

実験手順: A mixture of 1-bromopinacolone (0.5 mL, 3.7 mmol) and NaN3 (0.48 g, 7.38 mmol) in 50 mL acetone was stirred overnight at room temperature. It was then poured into brine and extracted with dichloromethane. The extracts were washed with brine, were dried over Na2SO4, filtered, and were evaporated to afford the title compound as a yellow oil (524 mg, 100%). 1H NMR (DMSO-d6) δ 4.39 (s, 2H), 1.10 (s, 9H); MS (DCI+) m/z 142 (M+H)+. extracted with dichloromethane The extracts were washed with brine were dried over Na2SO4 filtered were evaporated

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

実験手順: To a solution of 1-bromo-3,3-dimethylbutan-2-one (50 g, 279 mmol) in acetone (400 mL) is added NaN3 (22 g, 335 mmol) at 0° C. The reaction mixture is warmed to room temperature for 7 h. The reaction mixture is filtered and the filtrate is concentrated. The residue is diluted with EtOAc and washed with water and brine. The organic layer is dried (Na2SO4) and concentrated to afford the title crude compound which is used in the next step without purification. The reaction mixture is filtered the filtrate is concentrated The residue is diluted with EtOAc washed with water and brine The organic layer is dried (Na2SO4) concentrated

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

実験手順: A mixture of 1-bromopinacolone (0.5 mL, 3.7 mmol) and NaN3 (0.48 g, 7.38 mmol) in 50 mL acetone was stirred overnight at room temperature. It was then poured into brine and extracted with dichloromethane. The extracts were washed with brine, were dried over Na2SO4, filtered, and were evaporated to afford the title compound as a yellow oil (524 mg, 100%). 1H NMR (DMSO-d6) δ 4.39 (s, 2H), 1.10 (s, 9H); MS (DCI+) m/z 142 (M+H)+. extracted with dichloromethane The extracts were washed with brine were dried over Na2SO4 filtered were evaporated

反応条件: temp:0.00; pressure:0.00; stir: