叔丁基二甲基硅烷醇

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

实验步骤: The mixture of [4-(tert-butyldimethylsilanyloxy)butyl](3-nitro-quinolin-4-yl)amine and tert-butyldimethylsilanol (110 g) from the previous step was dissolved in toluene (880 mL) and placed in a Parr hydrogenation vessel along with 5% platinum on carbon catalyst (3.0 g). The vessel was pressurized to 50 psi (3.4×105 Pa) hydrogen and shaken on the Parr apparatus for 1.5 hours, occasionally adding additional hydrogen to maintain a pressure of 50 psi (3.4×105 Pa). After 3 hours, the reaction mixture was filtered through CELITE filter agent and concentrated under reduced pressure to provide N4-[4-(tert-butyldimethylsilanyloxy)butyl]quinoline-3,4-diamine as a dark oil that was used directly in the next step without further purification. to maintain a pressure of 50 psi (3.4×105 Pa) After 3 hours the reaction mixture was filtered through CELITE filter agent concentrated under reduced pressure

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

实验步骤: The mixture of [4-(tert-butyldimethylsilanyloxy)butyl](3-nitro-quinolin-4-yl)amine and tert-butyldimethylsilanol (110 g) from the previous step was dissolved in toluene (880 mL) and placed in a Parr hydrogenation vessel along with 5% platinum on carbon catalyst (3.0 g). The vessel was pressurized to 50 psi (3.4×105 Pa) hydrogen and shaken on the Parr apparatus for 1.5 hours, occasionally adding additional hydrogen to maintain a pressure of 50 psi (3.4×105 Pa). After 3 hours, the reaction mixture was filtered through CELITE filter agent and concentrated under reduced pressure to provide N4-[4-(tert-butyldimethylsilanyloxy)butyl]quinoline-3,4-diamine as a dark oil that was used directly in the next step without further purification. to maintain a pressure of 50 psi (3.4×105 Pa) After 3 hours the reaction mixture was filtered through CELITE filter agent concentrated under reduced pressure

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

实验步骤: The mixture of [4-(tert-butyldimethylsilanyloxy)butyl](3-nitro-quinolin-4-yl)amine and tert-butyldimethylsilanol (110 g) from the previous step was dissolved in toluene (880 mL) and placed in a Parr hydrogenation vessel along with 5% platinum on carbon catalyst (3.0 g). The vessel was pressurized to 50 psi (3.4×105 Pa) hydrogen and shaken on the Parr apparatus for 1.5 hours, occasionally adding additional hydrogen to maintain a pressure of 50 psi (3.4×105 Pa). After 3 hours, the reaction mixture was filtered through CELITE filter agent and concentrated under reduced pressure to provide N4-[4-(tert-butyldimethylsilanyloxy)butyl]quinoline-3,4-diamine as a dark oil that was used directly in the next step without further purification. to maintain a pressure of 50 psi (3.4×105 Pa) After 3 hours the reaction mixture was filtered through CELITE filter agent concentrated under reduced pressure

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

实验步骤: The mixture of [4-(tert-butyldimethylsilanyloxy)butyl](3-nitro-quinolin-4-yl)amine and tert-butyldimethylsilanol (110 g) from the previous step was dissolved in toluene (880 mL) and placed in a Parr hydrogenation vessel along with 5% platinum on carbon catalyst (3.0 g). The vessel was pressurized to 50 psi (3.4×105 Pa) hydrogen and shaken on the Parr apparatus for 1.5 hours, occasionally adding additional hydrogen to maintain a pressure of 50 psi (3.4×105 Pa). After 3 hours, the reaction mixture was filtered through CELITE filter agent and concentrated under reduced pressure to provide N4-[4-(tert-butyldimethylsilanyloxy)butyl]quinoline-3,4-diamine as a dark oil that was used directly in the next step without further purification. to maintain a pressure of 50 psi (3.4×105 Pa) After 3 hours the reaction mixture was filtered through CELITE filter agent concentrated under reduced pressure

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

实验步骤: The mixture of [4-(tert-butyldimethylsilanyloxy)butyl](3-nitro-quinolin-4-yl)amine and tert-butyldimethylsilanol (110 g) from the previous step was dissolved in toluene (880 mL) and placed in a Parr hydrogenation vessel along with 5% platinum on carbon catalyst (3.0 g). The vessel was pressurized to 50 psi (3.4×105 Pa) hydrogen and shaken on the Parr apparatus for 1.5 hours, occasionally adding additional hydrogen to maintain a pressure of 50 psi (3.4×105 Pa). After 3 hours, the reaction mixture was filtered through CELITE filter agent and concentrated under reduced pressure to provide N4-[4-(tert-butyldimethylsilanyloxy)butyl]quinoline-3,4-diamine as a dark oil that was used directly in the next step without further purification. to maintain a pressure of 50 psi (3.4×105 Pa) After 3 hours the reaction mixture was filtered through CELITE filter agent concentrated under reduced pressure

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

实验步骤: Trifluoroacetic acid (154 μl) was added to a solution of (4R)-4-t-butyldimethylsilyloxy-2-cyclopenten-1-one (5.79 g, 27.3 mmol) and benzylbutoxymethyltrimethylsilylmethylamine (15.4 g, 55.0 mmol) in dichloromethane (100 ml) at room temperature, followed by stirring for 20 minutes. A saturated sodium hydrogencarbonate aqueous solution was added to the reaction mixture, and the mixture was extracted with ethyl acetate. The organic layer was washed with a saturated sodium chloride aqueous solution and dried over anhydrous sodium sulfate. After removing the solvent by evaporation, the residue was purified by silica gel column chromatography (n-hexane:ethyl acetate=1:1) to give 4.21 g (19.7 mmol, 72%) of the title compound as a colorless oily substance. (1R,4R,5S)-7-Benzyl-4-t-butyldimethylsilyloxy-2-oxo-7-azabicyclo[3.3.0]octane was also obtained as a mixture with t-butyldimethylsilanol (3.10 g). The resulting mixture (3.10 g) of (1R,4R,5S)-7-benzyl-4-t-butyldimethylsilyloxy-2-oxo-7-azabicyclo[3.3.0]octane and t-butyldimethylsilanol was dissolved in tetrahydrofuran (30 ml), and a 1 M tetrahydrofuran solution (15 ml) of tetrabutylammonium fluoride was added thereto under cooling with ice, followed by stirring at room temperature for 20 minutes. The reaction mixture was poured into water and extracted with ethyl acetate. The organic layer was washed with a saturated sodium chloride aqueous solution and dried over anhydrous sodium sulfate. The solvent was removed by evaporation, and the residue was purified by silica gel column chromatography (n-hexane:ethyl acetate=1:1) to give 1.57 g (7.34 mmol) of the title compound as a colorless oily substance. under cooling with ice extracted with ethyl acetate The organic layer was washed with a saturated sodium chloride aqueous solution dried over anhydrous sodium sulfate The solvent was removed by evaporation the residue was purified by silica gel column chromatography (n-hexane:ethyl acetate=1:1)

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

实验步骤: The mixture of [4-(tert-butyldimethylsilanyloxy)butyl](3-nitro-quinolin-4-yl)amine and tert-butyldimethylsilanol (110 g) from the previous step was dissolved in toluene (880 mL) and placed in a Parr hydrogenation vessel along with 5% platinum on carbon catalyst (3.0 g). The vessel was pressurized to 50 psi (3.4×105 Pa) hydrogen and shaken on the Parr apparatus for 1.5 hours, occasionally adding additional hydrogen to maintain a pressure of 50 psi (3.4×105 Pa). After 3 hours, the reaction mixture was filtered through CELITE filter agent and concentrated under reduced pressure to provide N4-[4-(tert-butyldimethylsilanyloxy)butyl]quinoline-3,4-diamine as a dark oil that was used directly in the next step without further purification. to maintain a pressure of 50 psi (3.4×105 Pa) After 3 hours the reaction mixture was filtered through CELITE filter agent concentrated under reduced pressure

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

实验步骤: Trifluoroacetic acid (154 μl) was added to a solution of (4R)-4-t-butyldimethylsilyloxy-2-cyclopenten-1-one (5.79 g, 27.3 mmol) and benzylbutoxymethyltrimethylsilylmethylamine (15.4 g, 55.0 mmol) in dichloromethane (100 ml) at room temperature, followed by stirring for 20 minutes. A saturated sodium hydrogencarbonate aqueous solution was added to the reaction mixture, and the mixture was extracted with ethyl acetate. The organic layer was washed with a saturated sodium chloride aqueous solution and dried over anhydrous sodium sulfate. After removing the solvent by evaporation, the residue was purified by silica gel column chromatography (n-hexane:ethyl acetate=1:1) to give 4.21 g (19.7 mmol, 72%) of the title compound as a colorless oily substance. (1R,4R,5S)-7-Benzyl-4-t-butyldimethylsilyloxy-2-oxo-7-azabicyclo[3.3.0]octane was also obtained as a mixture with t-butyldimethylsilanol (3.10 g). The resulting mixture (3.10 g) of (1R,4R,5S)-7-benzyl-4-t-butyldimethylsilyloxy-2-oxo-7-azabicyclo[3.3.0]octane and t-butyldimethylsilanol was dissolved in tetrahydrofuran (30 ml), and a 1 M tetrahydrofuran solution (15 ml) of tetrabutylammonium fluoride was added thereto under cooling with ice, followed by stirring at room temperature for 20 minutes. The reaction mixture was poured into water and extracted with ethyl acetate. The organic layer was washed with a saturated sodium chloride aqueous solution and dried over anhydrous sodium sulfate. The solvent was removed by evaporation, and the residue was purified by silica gel column chromatography (n-hexane:ethyl acetate=1:1) to give 1.57 g (7.34 mmol) of the title compound as a colorless oily substance. under cooling with ice extracted with ethyl acetate The organic layer was washed with a saturated sodium chloride aqueous solution dried over anhydrous sodium sulfate The solvent was removed by evaporation the residue was purified by silica gel column chromatography (n-hexane:ethyl acetate=1:1)

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

实验步骤: The mixture of [4-(tert-butyldimethylsilanyloxy)butyl](3-nitro-quinolin-4-yl)amine and tert-butyldimethylsilanol (110 g) from the previous step was dissolved in toluene (880 mL) and placed in a Parr hydrogenation vessel along with 5% platinum on carbon catalyst (3.0 g). The vessel was pressurized to 50 psi (3.4×105 Pa) hydrogen and shaken on the Parr apparatus for 1.5 hours, occasionally adding additional hydrogen to maintain a pressure of 50 psi (3.4×105 Pa). After 3 hours, the reaction mixture was filtered through CELITE filter agent and concentrated under reduced pressure to provide N4-[4-(tert-butyldimethylsilanyloxy)butyl]quinoline-3,4-diamine as a dark oil that was used directly in the next step without further purification. to maintain a pressure of 50 psi (3.4×105 Pa) After 3 hours the reaction mixture was filtered through CELITE filter agent concentrated under reduced pressure