2-azidocyclohexan-1-ol

反应条件: temp:0.00; pressure:0.00; stir:

反应条件: temp:0.00; pressure:0.00; stir:

反应条件: temp:75.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

实验步骤: A solution of cyclohexene oxide (10.1 g, 103 mmol) and sodium azide (16.7 g, 257 mmol) in 100 mL of a 1:1 mixture of acetone:water was heated to reflux at 75° C. for 14 h. The mixture was cooled to rt, concentrated in vacuo to 50 mL, and extracted 3× with dichloromethane. The combined organic fractions were washed 2× with water, dried over sodium sulfate, filtered, and concentrated in vacuo to provide 2-azidocyclohexanol that gave a proton NMR spectra consistent with theory. The mixture was cooled to rt concentrated in vacuo to 50 mL extracted 3× with dichloromethane The combined organic fractions were washed 2× with water dried over sodium sulfate filtered concentrated in vacuo

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

实验步骤: To a solution of 2-azidocyclohexylalcohol (1 g, 7.1 mmol) in THF (10 mL), sodium hydride (284 mg, 7.1 mmol) was added. After 10 minutes, benzyl bromide (0.84 mL, 7.1 mmol) was added. The reaction mixture was partitioned between ethyl acetate and NaHCO3 (aq.). The organic layer was dried over MgSO4, filtered and concentrated under reduced pressure and chromatography of the resulting liquid on silica gel (hexane: ethyl acetate; 10:1) gave product (1.4 g, 85%). EI-MS m/z 232 (M+H)+. The reaction mixture was partitioned between ethyl acetate and NaHCO3 (aq.) The organic layer was dried over MgSO4 filtered concentrated under reduced pressure and chromatography of the resulting liquid on silica gel (hexane: ethyl acetate; 10:1)

反应条件: temp:72.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

实验步骤: A mixture of cyclohexene oxide (2 g, 20.4 mmol), sodium azide (1.86 g, 30.6 mmol), and ammonium chloride (2.16 g, 40.8 mmol) in methanol/water (61 mL/6 mL) was heated to 72° C. for 16 hours. The reaction mixture was then partitioned between ethyl acetate and water. The organic layer was dried over MgSO4, filtered and concentrated under reduced pressure to give pure product. (2.3 g, 80%). EI-MS m/z 242 (M+H)+. The reaction mixture was then partitioned between ethyl acetate and water The organic layer was dried over MgSO4 filtered concentrated under reduced pressure to give pure product

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

实验步骤: To a solution of 7-oxa-bicyclo[4.1.0]heptane (0.300 g, 3.06 mmol) in acetone (3 mL) was added sodium azide (0.504 g, 7.75 mmol) in water (3 mL). The reaction mixture was refluxed for 12 h. The acetone was removed in vacuo and the product was extracted with ethyl acetate (5 mL). The organic layer was collected, dried over anhydrous sodium sulfate, filtered, and concentrated to provide the title compound (46 mg). The reaction mixture was refluxed for 12 h The acetone was removed in vacuo the product was extracted with ethyl acetate (5 mL) The organic layer was collected dried over anhydrous sodium sulfate filtered concentrated

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

实验步骤: The azide (171.8 g, 1.22 mol) and tetrabutylammonium hydrogensulfate (4.2 g, 12.4 mmol) are sequentially added to a solution of methylene chloride (700 ml) and a 50% w/w aqueous solution of sodium hydroxide (129 g in 129 ml of water). The resulting mixture is vigorously stirred for 30 minutes before being cooled to 0° C. Dimethyl sulfate (186 g, 140 ml, 1.48 mol) is added in a dropwise manner to the vigorously stirred solution over a period of one hour, during which time a solid mass forms. This is broken up by addition of a further portion of methylene chloride (150 ml). The reaction mixture is then allowed to warm to room temperature and stirred for 20 hours. TLC analysis indicates a small amount of alcohol still remaining, and thus the reaction is allowed to proceed for an additional 12 hours at 50° C. After cooling to room temperature, the reaction is quenched by addition of concentrated ammonium hydroxide solution (100 ml) and allowed to stir for 45 minutes. The mixture is poured into water (500 ml) and extracted with methylene chloride (2×500 ml). The organic extracts are washed with water (3×500 ml) until the washings are neutral. The extracts are dried over sodium sulfate and the volatiles removed in vacuo. The crude product is passed through a plug of silica eluting with hexanes:ethyl acetate (9:1) to yield 1-azido-2-methoxycyclohexane (110 g, 58%) as a colorless oil. to warm to room temperature stirred for 20 hours to proceed for an additional 12 hours at 50° C After cooling to room temperature the reaction is quenched by addition of concentrated ammonium hydroxide solution (100 ml) to stir for 45 minutes The mixture is poured into water (500 ml) extracted with methylene chloride (2×500 ml) The organic extracts are washed with water (3×500 ml) until the washings The extracts are dried over sodium sulfate the volatiles removed in vacuo

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

实验步骤: The azide (171.8 g, 1.22 mol) and tetrabutylammonium hydrogensulfate (4.2 g, 12.4 mmol) are sequentially added to a solution of methylene chloride (700 ml) and a 50% w/w aqueous solution of sodium hydroxide (129 g in 129 ml of water). The resulting mixture is vigorously stirred for 30 minutes before being cooled to 0° C. Dimethyl sulfate (186 g, 140 ml, 1.48 mol) is added in a dropwise manner to the vigorously stirred solution over a period of one hour, during which time a solid mass forms. This is broken up by addition of a further portion of methylene chloride (150 ml). The reaction mixture is then allowed to warm to room temperature and stirred for 20 hours. TLC analysis indicates a small amount of alcohol still remaining, and thus the reaction is allowed to proceed for an additional 12 hours at 50° C. After cooling to room temperature, the reaction is quenched by addition of concentrated ammonium hydroxide solution (100 ml) and allowed to stir for 45 minutes. The mixture is poured into water (500 ml) and extracted with methylene chloride (2×500 ml). The organic extracts are washed with water (3×500 ml) until the washings are neutral. The extracts are dried over sodium sulfate and the volatiles removed in vacuo. The crude product is passed through a plug of silica eluting with hexanes:ethyl acetate (9:1) to yield 1-azido-2-methoxycyclohexane (110 g, 58%) as a colorless oil. to warm to room temperature stirred for 20 hours to proceed for an additional 12 hours at 50° C After cooling to room temperature the reaction is quenched by addition of concentrated ammonium hydroxide solution (100 ml) to stir for 45 minutes The mixture is poured into water (500 ml) extracted with methylene chloride (2×500 ml) The organic extracts are washed with water (3×500 ml) until the washings The extracts are dried over sodium sulfate the volatiles removed in vacuo

反应条件: temp:50.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

实验步骤: To a solution of cyclohexene oxide (150 g, 1.53 mol) in a mixture of ethanol (600 ml) and water (600 ml) is added ammonium chloride (168 g, 3.1 mol) followed by sodium azide (198 g, 3 mol). The resulting solution is stirred gently at 50° C. for 12 hours before being allowed to cool. The volatiles are removed in vacuo, and 6M hydrochloric acid (˜120 ml) is added to bring the reaction to pH 7. The reaction is extracted with ethyl acetate (2×750 ml), and the organic extracts are washed with brine (750 ml) and dried over sodium sulfate. Removal of the solvent in vacuo affords 2-azido-cyclohexan-1-ol as a slightly yellow oil (171.8 g, 80%), which is used in the following step without further purification. to cool The volatiles are removed in vacuo, and 6M hydrochloric acid (˜120 ml) is added the reaction to pH 7 The reaction is extracted with ethyl acetate (2×750 ml) the organic extracts are washed with brine (750 ml) dried over sodium sulfate Removal of the solvent in vacuo

反应条件: temp:75.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

实验步骤: A solution of cyclohexene oxide (10.1 g, 103 mmol) and sodium azide (16.7 g, 257 mmol) in 100 mL of a 1:1 mixture of acetone:water was heated to reflux at 75° C. for 14 h. The mixture was cooled to rt, concentrated in vacuo to 50 mL, and extracted 3× with dichloromethane. The combined organic fractions were washed 2× with water, dried over sodium sulfate, filtered, and concentrated in vacuo to provide 2-azidocyclohexanol that gave a proton NMR spectra consistent with theory. The mixture was cooled to rt concentrated in vacuo to 50 mL extracted 3× with dichloromethane The combined organic fractions were washed 2× with water dried over sodium sulfate filtered concentrated in vacuo

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

实验步骤: To a solution of 2-azidocyclohexylalcohol (1 g, 7.1 mmol) in THF (10 mL), sodium hydride (284 mg, 7.1 mmol) was added. After 10 minutes, benzyl bromide (0.84 mL, 7.1 mmol) was added. The reaction mixture was partitioned between ethyl acetate and NaHCO3 (aq.). The organic layer was dried over MgSO4, filtered and concentrated under reduced pressure and chromatography of the resulting liquid on silica gel (hexane: ethyl acetate; 10:1) gave product (1.4 g, 85%). EI-MS m/z 232 (M+H)+. The reaction mixture was partitioned between ethyl acetate and NaHCO3 (aq.) The organic layer was dried over MgSO4 filtered concentrated under reduced pressure and chromatography of the resulting liquid on silica gel (hexane: ethyl acetate; 10:1)

反应条件: temp:72.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

实验步骤: A mixture of cyclohexene oxide (2 g, 20.4 mmol), sodium azide (1.86 g, 30.6 mmol), and ammonium chloride (2.16 g, 40.8 mmol) in methanol/water (61 mL/6 mL) was heated to 72° C. for 16 hours. The reaction mixture was then partitioned between ethyl acetate and water. The organic layer was dried over MgSO4, filtered and concentrated under reduced pressure to give pure product. (2.3 g, 80%). EI-MS m/z 242 (M+H)+. The reaction mixture was then partitioned between ethyl acetate and water The organic layer was dried over MgSO4 filtered concentrated under reduced pressure to give pure product