7-oxaspiro[3.5]nonan-8-one

Conditions: temp:0.00; pressure:0.00; stir:

Conditions: temp:0.00; pressure:0.00; stir:

Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: To a solution of 7-oxaspiro[3.5]nonan-6-one (0.67 g) in tetrahedrofuran (3 mL) cooled at −78° C. was added 1M diisobutylaluminum hydride/tetrahydrofuran (1.0 mL) dropwise over 5 minutes. The reaction solution was stirred at that temperature for 1.5 hours. Water (40 μL) was added to the reaction solution. After allowing the temperature to rise to room temperature, a 15% aqueous sodium hydroxide solution (40 μL) and water (120 μL) were successively added to the solution. After stirring the solution at room temperature for 10 minutes, diethyl ether (2 mL) and anhydrous magnesium sulfate (0.17 g) were added. The solution was stirred for additional 30 minutes. The reaction solution was then filtered with Celite. The filtrate was concentrated under reduced pressure to give the title compound (230 mg). to rise to room temperature After stirring the solution at room temperature for 10 minutes The solution was stirred for additional 30 minutes The reaction solution was then filtered with Celite The filtrate was concentrated under reduced pressure

Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: To a solution of 7-oxaspiro[3.5]nonan-6-one (0.67 g) in tetrahedrofuran (3 mL) cooled at −78° C. was added 1M diisobutylaluminum hydride/tetrahydrofuran (1.0 mL) dropwise over 5 minutes. The reaction solution was stirred at that temperature for 1.5 hours. Water (40 μL) was added to the reaction solution. After allowing the temperature to rise to room temperature, a 15% aqueous sodium hydroxide solution (40 μL) and water (120 μL) were successively added to the solution. After stirring the solution at room temperature for 10 minutes, diethyl ether (2 mL) and anhydrous magnesium sulfate (0.17 g) were added. The solution was stirred for additional 30 minutes. The reaction solution was then filtered with Celite. The filtrate was concentrated under reduced pressure to give the title compound (230 mg). to rise to room temperature After stirring the solution at room temperature for 10 minutes The solution was stirred for additional 30 minutes The reaction solution was then filtered with Celite The filtrate was concentrated under reduced pressure

Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: To a solution of 7-oxaspiro[3.5]nonan-6-one (0.67 g) in tetrahedrofuran (3 mL) cooled at −78° C. was added 1M diisobutylaluminum hydride/tetrahydrofuran (1.0 mL) dropwise over 5 minutes. The reaction solution was stirred at that temperature for 1.5 hours. Water (40 μL) was added to the reaction solution. After allowing the temperature to rise to room temperature, a 15% aqueous sodium hydroxide solution (40 μL) and water (120 μL) were successively added to the solution. After stirring the solution at room temperature for 10 minutes, diethyl ether (2 mL) and anhydrous magnesium sulfate (0.17 g) were added. The solution was stirred for additional 30 minutes. The reaction solution was then filtered with Celite. The filtrate was concentrated under reduced pressure to give the title compound (230 mg). to rise to room temperature After stirring the solution at room temperature for 10 minutes The solution was stirred for additional 30 minutes The reaction solution was then filtered with Celite The filtrate was concentrated under reduced pressure

Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: To an ice-cooled solution of methyl (1-vinylcyclobutyl)acetate (0.67 g) in tetrahydrofuran (3 mL) was added 0.5M9-borabicyclo[3.3.1]nonane/tetrahydrofuran (17.5 mL) dropwise over 10 minutes. The reaction solution was then allowed for its temperature to rise to room temperature and it was stirred for additional 9 hours. The reaction solution was again ice-cooled and ethanol (4 mL), a 6N aqueous sodium hydroxide solution (8 mL) and 30% hydrogen peroxide (8 mL) were successively added thereto. The reaction solution was then allowed for its temperature to rise to room temperature and it was stirred for additional 30 minutes. The reaction solution was again ice-cooled. After conc. hydrochloric acid (5 mL) was added to the solution, it was stirred for additional 30 minutes. The reaction solution was extracted with tert-butyl methyl ether. The organic layer was washed with saturated aqueous sodium chloride solution, dried over anhydrous sodium sulfate and concentrated under reduced pressure. The resulting residue was purified by chromatography [silica gel, hexane-ethyl acetate (9:1)] to give the title compound (0.31 g). was added 0 to rise to room temperature cooled to rise to room temperature it was stirred for additional 30 minutes cooled was stirred for additional 30 minutes The reaction solution was extracted with tert-butyl methyl ether The organic layer was washed with saturated aqueous sodium chloride solution dried over anhydrous sodium sulfate concentrated under reduced pressure The resulting residue was purified by chromatography [silica gel, hexane-ethyl acetate (9:1)]

Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: To an ice-cooled solution of methyl (1-vinylcyclobutyl)acetate (0.67 g) in tetrahydrofuran (3 mL) was added 0.5M9-borabicyclo[3.3.1]nonane/tetrahydrofuran (17.5 mL) dropwise over 10 minutes. The reaction solution was then allowed for its temperature to rise to room temperature and it was stirred for additional 9 hours. The reaction solution was again ice-cooled and ethanol (4 mL), a 6N aqueous sodium hydroxide solution (8 mL) and 30% hydrogen peroxide (8 mL) were successively added thereto. The reaction solution was then allowed for its temperature to rise to room temperature and it was stirred for additional 30 minutes. The reaction solution was again ice-cooled. After conc. hydrochloric acid (5 mL) was added to the solution, it was stirred for additional 30 minutes. The reaction solution was extracted with tert-butyl methyl ether. The organic layer was washed with saturated aqueous sodium chloride solution, dried over anhydrous sodium sulfate and concentrated under reduced pressure. The resulting residue was purified by chromatography [silica gel, hexane-ethyl acetate (9:1)] to give the title compound (0.31 g). was added 0 to rise to room temperature cooled to rise to room temperature it was stirred for additional 30 minutes cooled was stirred for additional 30 minutes The reaction solution was extracted with tert-butyl methyl ether The organic layer was washed with saturated aqueous sodium chloride solution dried over anhydrous sodium sulfate concentrated under reduced pressure The resulting residue was purified by chromatography [silica gel, hexane-ethyl acetate (9:1)]

Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: To an ice-cooled solution of methyl (1-vinylcyclobutyl)acetate (0.67 g) in tetrahydrofuran (3 mL) was added 0.5M9-borabicyclo[3.3.1]nonane/tetrahydrofuran (17.5 mL) dropwise over 10 minutes. The reaction solution was then allowed for its temperature to rise to room temperature and it was stirred for additional 9 hours. The reaction solution was again ice-cooled and ethanol (4 mL), a 6N aqueous sodium hydroxide solution (8 mL) and 30% hydrogen peroxide (8 mL) were successively added thereto. The reaction solution was then allowed for its temperature to rise to room temperature and it was stirred for additional 30 minutes. The reaction solution was again ice-cooled. After conc. hydrochloric acid (5 mL) was added to the solution, it was stirred for additional 30 minutes. The reaction solution was extracted with tert-butyl methyl ether. The organic layer was washed with saturated aqueous sodium chloride solution, dried over anhydrous sodium sulfate and concentrated under reduced pressure. The resulting residue was purified by chromatography [silica gel, hexane-ethyl acetate (9:1)] to give the title compound (0.31 g). was added 0 to rise to room temperature cooled to rise to room temperature it was stirred for additional 30 minutes cooled was stirred for additional 30 minutes The reaction solution was extracted with tert-butyl methyl ether The organic layer was washed with saturated aqueous sodium chloride solution dried over anhydrous sodium sulfate concentrated under reduced pressure The resulting residue was purified by chromatography [silica gel, hexane-ethyl acetate (9:1)]