2-苄基-四氢吡咯并[3,4-C]吡咯-1,3-二酮

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:0.00; pressure:0.00; stir:

反应条件: temp:0.00; pressure:0.00; stir:

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

实验步骤: A solution of lithium aluminum hydride (15.0 mL, 1.0 M solution in ether) was added dropwise to a solution of compound 2 (1.15 g) in THF (50 mL) and dichloromethane (40 mL) at 0° C. The reaction mixture was stirred an additional 1.5 hour at 0° C. and water (0.5 mL) was added followed by the addition of aqueous NaOH solution (0.5 mL, 20%) and then water (1.5 mL). The resulting solids was filtered off and the filtrate was concentrated in vacuo. The residue was purified by flash chromatography to provide the title compound 3 as a pale yellow oil (0.93 g, 92%). LCMS: Rf: 0.368 min, M+H+: 203. The resulting solids was filtered off the filtrate was concentrated in vacuo The residue was purified by flash chromatography

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

实验步骤: 1-Chloroethylchloroformate (3.24 mL) was added dropwise to a solution of compound 1 (5.22 g) in dichloromethane (75 mL) at 0° C. The solution was then heated to reflux for 3 hours, cooled to room temperature and concentrated in vacuo. The residue was then dissolved in methanol (75 mL) and heated to reflux for another 3 hours. The mixture was cooled to 0° C. and ether (200 mL) was added. Filtration afforded the title compound 2 as a white solid (3.38 g, 90%). LCMS: Rf: 0.380 min, M+H+: 231. The solution was then heated to reflux for 3 hours concentrated in vacuo The residue was then dissolved in methanol (75 mL) heated to reflux for another 3 hours The mixture was cooled to 0° C. ether (200 mL) was added Filtration

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

实验步骤: A solution of lithium aluminum hydride (15.0 mL, 1.0 M solution in ether) was added dropwise to a solution of compound 2 (1.15 g) in THF (50 mL) and dichloromethane (40 mL) at 0° C. The reaction mixture was stirred an additional 1.5 hour at 0° C. and water (0.5 mL) was added followed by the addition of aqueous NaOH solution (0.5 mL, 20%) and then water (1.5 mL). The resulting solids was filtered off and the filtrate was concentrated in vacuo. The residue was purified by flash chromatography to provide the title compound 3 as a pale yellow oil (0.93 g, 92%). LCMS: Rf: 0.368 min, M+H+: 203. The resulting solids was filtered off the filtrate was concentrated in vacuo The residue was purified by flash chromatography

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

实验步骤: 1-Chloroethylchloroformate (3.24 mL) was added dropwise to a solution of compound 1 (5.22 g) in dichloromethane (75 mL) at 0° C. The solution was then heated to reflux for 3 hours, cooled to room temperature and concentrated in vacuo. The residue was then dissolved in methanol (75 mL) and heated to reflux for another 3 hours. The mixture was cooled to 0° C. and ether (200 mL) was added. Filtration afforded the title compound 2 as a white solid (3.38 g, 90%). LCMS: Rf: 0.380 min, M+H+: 231. The solution was then heated to reflux for 3 hours concentrated in vacuo The residue was then dissolved in methanol (75 mL) heated to reflux for another 3 hours The mixture was cooled to 0° C. ether (200 mL) was added Filtration

反应条件: temp:70.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

实验步骤: Lithium aluminium hydride (1M in THF, 85 ml, 85 mmol) was added slowly to a stirred solution of 2-benzyl-tetrahydro-pyrrolo[3,4-c]pyrrole-1,3-dione (6.4 g, 27.8 mmol) in dry tetrahydrofuran (60 ml) at room temperature under nitrogen. Upon complete addition, the mixture was stirred and heated at 70° C. for 16 h. The mixture was then cooled to 0° C. and carefully quenched with water (3.2 ml), followed by 4N sodium hydroxide (3.2 ml) and water (4.5 ml). The mixture was filtered, washing with ethyl acetate. The filtrate was evaporated and the residue was purified by chromatography on silica gel, eluting with CH2Cl2 /MeOH/NH3 (40:8:1→30:8:1) to give the title amine (4.5 g, 80%) as a clear oil. 1H NMR δ (360 MHz, CDCl3) 2.24-2.28 (2H, m), 2.42 (1H, s), 2.56-2.64 (4H, m), 2.68 (1H, dd, J=11.5. 2.4 Hz), 2.77-2.83 (2H, m), 3.44 (2H, s, CH2Ph), 7.13-7.30 (5H, m, Ar--H). 13C NMR δ (90.5 MHz, CDCl3) 43.6 (CH), 54.4 (CH2), 59.9 (CH2), 60.8 (CH2), 126.8 (CH), 128.2 (CH), 128.8 (CH), 139.3 (C). Upon complete addition The mixture was then cooled to 0° C. carefully quenched with water (3.2 ml) The mixture was filtered washing with ethyl acetate The filtrate was evaporated the residue was purified by chromatography on silica gel eluting with CH2Cl2 /MeOH/NH3 (40:8:1→30:8:1)