2-azabicyclo[3.3.1]nonane

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 solution (6.5 ml) of 2-azabicyclo[3.3.1]nonane (100 mg, 0.62 mmol) in dimethoxyethane were added allylbromide (105 mg, 0.87 mmol) and potassium carbonate (94 mg, 0.68 mmol) and the mixture was heated at reflux temperature for 3.5 hours. Ether (10 ml) was added to the reaction mixture, followed by filtration and removal of the solvent, and the residue was purified with silica gel column chromatography (chloroform-methanol-triethylamine=100:9:1), to obtain 2-allyl-2-azabicyclo[3.3.1]nonane (52 mg, 51%) as a colorless oily substance. the mixture was heated at reflux temperature for 3.5 hours followed by filtration and removal of the solvent the residue was purified with silica gel column chromatography (chloroform-methanol-triethylamine=100:9:1)

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

実験手順: To a solution (2 ml) of 2-azabicyclo[3.3.1]nonane (100 mg, 0.62 mmol) in methanol were added a 10% acetaldehyde solution (5 ml) and 10% palladium on activated carbon (100 mg) and the mixture was stirred for 3 hours under the hydrogen atmosphere. The reaction mixture was filtered by means of suction, and the filtrate was concentrated under a reduced pressure. A saturated aqueous solution of sodium bicarbonate (10 ml) was added to the residue, followed by extraction with chloroform (3×20 ml). The extrant was dried (over MgSO4), followed by removal of the solvent and purification of the residue with silica gel column chromatography (chloroform-methanol-triethylamine=100:9:1), to obtain 2-ethyl-2-azabicyclo[3.3.1]nonane (68 mg, 72%) as a colorless oily material. The reaction mixture was filtered by means of suction the filtrate was concentrated under a reduced pressure A saturated aqueous solution of sodium bicarbonate (10 ml) was added to the residue followed by extraction with chloroform (3×20 ml) The extrant was dried (over MgSO4) followed by removal of the solvent and purification of the residue with silica gel column chromatography (chloroform-methanol-triethylamine=100:9:1)

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

実験手順: To a solution (6.5 ml) of 2-azabicyclo[3.3.1]nonane (100 mg, 0.62 mmol) in dimethoxyethane were added allylbromide (105 mg, 0.87 mmol) and potassium carbonate (94 mg, 0.68 mmol) and the mixture was heated at reflux temperature for 3.5 hours. Ether (10 ml) was added to the reaction mixture, followed by filtration and removal of the solvent, and the residue was purified with silica gel column chromatography (chloroform-methanol-triethylamine=100:9:1), to obtain 2-allyl-2-azabicyclo[3.3.1]nonane (52 mg, 51%) as a colorless oily substance. the mixture was heated at reflux temperature for 3.5 hours followed by filtration and removal of the solvent the residue was purified with silica gel column chromatography (chloroform-methanol-triethylamine=100:9:1)

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

実験手順: To a solution (2 ml) of 2-azabicyclo[3.3.1]nonane (100 mg, 0.62 mmol) in methanol were added a 10% acetaldehyde solution (5 ml) and 10% palladium on activated carbon (100 mg) and the mixture was stirred for 3 hours under the hydrogen atmosphere. The reaction mixture was filtered by means of suction, and the filtrate was concentrated under a reduced pressure. A saturated aqueous solution of sodium bicarbonate (10 ml) was added to the residue, followed by extraction with chloroform (3×20 ml). The extrant was dried (over MgSO4), followed by removal of the solvent and purification of the residue with silica gel column chromatography (chloroform-methanol-triethylamine=100:9:1), to obtain 2-ethyl-2-azabicyclo[3.3.1]nonane (68 mg, 72%) as a colorless oily material. The reaction mixture was filtered by means of suction the filtrate was concentrated under a reduced pressure A saturated aqueous solution of sodium bicarbonate (10 ml) was added to the residue followed by extraction with chloroform (3×20 ml) The extrant was dried (over MgSO4) followed by removal of the solvent and purification of the residue with silica gel column chromatography (chloroform-methanol-triethylamine=100:9:1)

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 solution (6.5 ml) of 2-azabicyclo[3.3.1]nonane (100 mg, 0.62 mmol) in dimethoxyethane were added allylbromide (105 mg, 0.87 mmol) and potassium carbonate (94 mg, 0.68 mmol) and the mixture was heated at reflux temperature for 3.5 hours. Ether (10 ml) was added to the reaction mixture, followed by filtration and removal of the solvent, and the residue was purified with silica gel column chromatography (chloroform-methanol-triethylamine=100:9:1), to obtain 2-allyl-2-azabicyclo[3.3.1]nonane (52 mg, 51%) as a colorless oily substance. the mixture was heated at reflux temperature for 3.5 hours followed by filtration and removal of the solvent the residue was purified with silica gel column chromatography (chloroform-methanol-triethylamine=100:9:1)

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

実験手順: To a solution (2 ml) of 2-azabicyclo[3.3.1]nonane (100 mg, 0.62 mmol) in methanol were added a 10% acetaldehyde solution (5 ml) and 10% palladium on activated carbon (100 mg) and the mixture was stirred for 3 hours under the hydrogen atmosphere. The reaction mixture was filtered by means of suction, and the filtrate was concentrated under a reduced pressure. A saturated aqueous solution of sodium bicarbonate (10 ml) was added to the residue, followed by extraction with chloroform (3×20 ml). The extrant was dried (over MgSO4), followed by removal of the solvent and purification of the residue with silica gel column chromatography (chloroform-methanol-triethylamine=100:9:1), to obtain 2-ethyl-2-azabicyclo[3.3.1]nonane (68 mg, 72%) as a colorless oily material. The reaction mixture was filtered by means of suction the filtrate was concentrated under a reduced pressure A saturated aqueous solution of sodium bicarbonate (10 ml) was added to the residue followed by extraction with chloroform (3×20 ml) The extrant was dried (over MgSO4) followed by removal of the solvent and purification of the residue with silica gel column chromatography (chloroform-methanol-triethylamine=100:9:1)

反応条件: temp:0.00; pressure:0.00; stir: