5-benzyl-2-methyltetrahydropyrrolo[3,4-c]pyrrole-1,3(2H,3aH)-dione

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:0.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

実験手順: N-Methylmaleimide (23.3 g, 21 mmol; Aldrich) was dissolved in CH2Cl2 (400 mL) in a 3-neck flask, chilled to 0° C. under nitrogen, and treated with trifluoroacetic acid (1.6 mL, 21 mmol; Aldrich). A solution of N-(methoxymethyl)-N-(trimethylsilylmethyl)-benzylamine (49.8 g, 21 mmol; Aldrich) in CH2Cl2 (60 mL) was then added slowly at a rate to maintain the temperature below about 5° C. After the addition was complete, the ice bath was removed and the reaction mixture was stirred for 24 h. The solution was concentrated under vacuum, and the residue was diluted with CH2Cl2 (125 mL), washed with saturated aqueous NaHCO3 (2×100 mL) and brine (2×100 mL). The organic phase was concentrated under vacuum to afford the title compound as a white solid (51.2 g, 21 mmol; 100% yield): 1H NMR (300 MHz, CDCl3) δ ppm 7.14-7.37 (m, 5H), 3.57 (s, 2H), 3.28 (d, J=10.2 Hz, 2H), 3.13-3.21 (m, 2H), 3.01 (s, 3H), 2.32-2.42 (m, 2H); MS (DCl/NH3) m/z 245 (M+H)+. to maintain the temperature below about 5° C After the addition the ice bath was removed The solution was concentrated under vacuum the residue was diluted with CH2Cl2 (125 mL) washed with saturated aqueous NaHCO3 (2×100 mL) and brine (2×100 mL) The organic phase was concentrated under vacuum

反応条件: temp:0.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

実験手順: N-Methylmaleimide (23.3 g, 21 mmol; Aldrich) was dissolved in CH2Cl2 (400 mL) in a 3-neck flask, chilled to 0° C. under nitrogen, and treated with trifluoroacetic acid (1.6 mL, 21 mmol; Aldrich). A solution of N-(methoxymethyl)-N-(trimethylsilylmethyl)-benzylamine (49.8 g, 21 mmol; Aldrich) in CH2Cl2 (60 mL) was then added slowly at a rate to maintain the temperature below about 5° C. After the addition was complete, the ice bath was removed and the reaction mixture was stirred for 24 h. The solution was concentrated under vacuum, and the residue was diluted with CH2Cl2 (125 mL), washed with saturated aqueous NaHCO3 (2×100 mL) and brine (2×100 mL). The organic phase was concentrated under vacuum to afford the title compound as a white solid (51.2 g, 21 mmol; 100% yield): 1H NMR (300 MHz, CDCl3) δ ppm 7.14-7.37 (m, 5H), 3.57 (s, 2H), 3.28 (d, J=10.2 Hz, 2H), 3.13-3.21 (m, 2H), 3.01 (s, 3H), 2.32-2.42 (m, 2H); MS (DCI/NH3) m/z 245 (M+H)+. to maintain the temperature below about 5° C After the addition the ice bath was removed The solution was concentrated under vacuum the residue was diluted with CH2Cl2 (125 mL) washed with saturated aqueous NaHCO3 (2×100 mL) and brine (2×100 mL) The organic phase was concentrated under vacuum

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:0.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

実験手順: Trifluoroacetic acid (2.4 g) was added dropwise to a solution of benzyl-methoxymethyltrimethylsilanylmethylamine (5.1 g) and 1-methylpyrrole-2,5-dione (2.98 g) in dichloromethane (50 ml) at 0° C. Stirring at 0° C. for 15 minutes was followed by further stirring at room temperature for one hour. The reaction mixture was diluted with dichloromethane, washed with sodium bicarbonate solution and water, dried over magnesium sulfate and concentrated. The product with the molecular weight of 244.30 (C14H16N2O2); MS (ESI): 245 (M+H+) was obtained in this way. by further stirring at room temperature for one hour washed with sodium bicarbonate solution and water dried over magnesium sulfate concentrated MS (ESI): 245 (M+H+) was obtained in this way

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

実験手順: A solution of 5-benzyl-2-methyltetrahydropyrrolo[3,4-c]pyrrole-1,3-dione (3.6 g) in THF (15 ml) was added dropwise to a suspension of lithium aluminum hydride (1.68 g) in THF (20 ml) while cooling in ice. The mixture was heated to reflux for 4 hours and then, at 0° C., water (1.8 ml), sodium hydroxide solution (10 M; 1.8 ml) and water (2.5 ml) were cautiously added. The precipitate was filtered off with suction and washed with ethyl acetate. The filtrate was concentrated. The product with the molecular weight of 216.33 (C14H20N2); MS (ESI): 217 (M+H+) was obtained in this way. while cooling in ice The mixture was heated to reflux for 4 hours The precipitate was filtered off with suction washed with ethyl acetate The filtrate was concentrated MS (ESI): 217 (M+H+) was obtained in this way

反応条件: temp:0.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

実験手順: Trifluoroacetic acid (2.4 g) was added dropwise to a solution of benzyl-methoxymethyltrimethylsilanylmethylamine (5.1 g) and 1-methylpyrrole-2,5-dione (2.98 g) in dichloromethane (50 ml) at 0° C. Stirring at 0° C. for 15 minutes was followed by further stirring at room temperature for one hour. The reaction mixture was diluted with dichloromethane, washed with sodium bicarbonate solution and water, dried over magnesium sulfate and concentrated. The product with the molecular weight of 244.30 (C14H16N2O2); MS (ESI): 245 (M+H+) was obtained in this way. by further stirring at room temperature for one hour washed with sodium bicarbonate solution and water dried over magnesium sulfate concentrated MS (ESI): 245 (M+H+) was obtained in this way

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

実験手順: A solution of 5-benzyl-2-methyltetrahydropyrrolo[3,4-c]pyrrole-1,3-dione (3.6 g) in THF (15 ml) was added dropwise to a suspension of lithium aluminum hydride (1.68 g) in THF (20 ml) while cooling in ice. The mixture was heated to reflux for 4 hours and then, at 0° C., water (1.8 ml), sodium hydroxide solution (10 M; 1.8 ml) and water (2.5 ml) were cautiously added. The precipitate was filtered off with suction and washed with ethyl acetate. The filtrate was concentrated. The product with the molecular weight of 216.33 (C14H2ON2); MS (ESI): 217 (M+H+) was obtained in this way. while cooling in ice The mixture was heated to reflux for 4 hours The precipitate was filtered off with suction washed with ethyl acetate The filtrate was concentrated MS (ESI): 217 (M+H+) was obtained in this way

反応条件: temp:0.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

実験手順: N-Methylmaleimide (23.3 g, 21 mmol; Aldrich) was dissolved in CH2Cl2 (400 mL) in a 3-neck flask, chilled to 0° C. under nitrogen, and treated with trifluoroacetic acid (1.6 mL, 21 mmol; Aldrich). A solution of N-(methoxymethyl)-N-(trimethylsilylmethyl)-benzylamine (49.8 g, 21 mmol; Aldrich) in CH2Cl2 (60 mL) was then added slowly at a rate to maintain the temperature below about 5° C. After the addition was complete, the ice bath was removed and the reaction mixture was stirred for 24 h. The solution was concentrated under vacuum, and the residue was diluted with CH2Cl2 (125 mL), washed with saturated aqueous NaHCO3 (2×100 mL) and brine (2×100 mL). The organic phase was concentrated under vacuum to afford the title compound as a white solid (51.2 g, 21 mmol; 100% yield): 1H NMR (300 MHz, CDCl3) δ ppm 7.14-7.37 (m, 5H), 3.57 (s, 2H), 3.28 (d, J=10.2 Hz, 2H), 3.13-3.21 (m, 2H), 3.01 (s, 3H), 2.32-2.42 (m, 2H); MS (DCl/NH3) m/z 245 (M+H)+. to maintain the temperature below about 5° C After the addition the ice bath was removed The solution was concentrated under vacuum the residue was diluted with CH2Cl2 (125 mL) washed with saturated aqueous NaHCO3 (2×100 mL) and brine (2×100 mL) The organic phase was concentrated under vacuum

反応条件: temp:0.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

実験手順: N-Methylmaleimide (23.3 g, 21 mmol; Aldrich) was dissolved in CH2Cl2 (400 mL) in a 3-neck flask, chilled to 0° C. under nitrogen, and treated with trifluoroacetic acid (1.6 mL, 21 mmol; Aldrich). A solution of N-(methoxymethyl)-N-(trimethylsilylmethyl)-benzylamine (49.8 g, 21 mmol; Aldrich) in CH2Cl2 (60 mL) was then added slowly at a rate to maintain the temperature below about 5° C. After the addition was complete, the ice bath was removed and the reaction mixture was stirred for 24 h. The solution was concentrated under vacuum, and the residue was diluted with CH2Cl2 (125 mL), washed with saturated aqueous NaHCO3 (2×100 mL) and brine (2×100 mL). The organic phase was concentrated under vacuum to afford the title compound as a white solid (51.2 g, 21 mmol; 100% yield): 1H NMR (300 MHz, CDCl3) δ ppm 7.14-7.37 (m, 5H), 3.57 (s, 2H), 3.28 (d, J=10.2 Hz, 2H), 3.13-3.21 (m, 2H), 3.01 (s, 3H), 2.32-2.42 (m, 2H); MS (DCI/NH3) m/z 245 (M+H)+. to maintain the temperature below about 5° C After the addition the ice bath was removed The solution was concentrated under vacuum the residue was diluted with CH2Cl2 (125 mL) washed with saturated aqueous NaHCO3 (2×100 mL) and brine (2×100 mL) The organic phase was concentrated under vacuum