rel-(3aR,7aS)-Hexahydro-1H-isoindole-1,3(2H)-dione

White crystalline powder

dd 30 g (0.20 mol) of phthalimide to a 1 L stainless steel magnetic stirring autoclave.A composite catalyst of 700 ml of methanol and 1.5 g of lanthanum chloride and copper powder supported alumina was used to seal the reaction vessel.After the air in the autoclave was replaced with nitrogen, the stirring was started to increase.When the temperature was raised to 250 ° C, the gauge pressure was 13.2 MPa. At this point, hydrogen is introduced.And pressurize to the pressure inside the kettle to 15Mpa. Insulation and pressure retention reaction for 30 hours, after the end of the heat preservation, Close the hydrogen inlet valve to cool to 10 ° C, After replacing the gas in the kettle with nitrogen, the liquid reaction solution was poured out. Filter, filter out the catalyst, The filtrate was transferred to a rotary evaporator.The methanol was distilled at atmospheric pressure, and after distilling off 600 ml of the distillate, the distillation was stopped. Cool to room temperature, A large amount of white granule crystals were precipitated, filtered through a Buchner funnel, and the filtrate and the distillate were combined.The filter cake was washed with 50 ml of water.The filter cake is dried to obtain 28.8 g of pure white crystalline powder, and the melting range is 138.8 ° C -140.3 ° C.The content of the liquid chromatographic analysis was 98.87percent. The selectivity of the reaction is 93.05percent, based on phthalimide.The yield was 94.11percent.General procedure: A mixture of a cyclic anhydride 1 (1 mmol), guanidiniumchloride (2) (1 mmol), Et3N (2 mmol) and FeCl3 (10 molpercent)in PEG-400 (0.5 mL) at 60°C for aromatic derivatives andat 100°C for aliphatic derivatives was stirred for an appropriatetime. The reaction progress was monitored by thinlayerchromatography. After the completion of the reaction, the reaction mixture was cooled to room temperature andthen was extracted with H2O and EtOAc. The organic layerwas dried over MgSO4 and then evaporated under reducedpressure. The residue was purified by column chromatographyon silica gel using n-hexane-EtOAc (7:3). The desired1H-isoindole-1, 3(2H)-diones were obtained in 70–95percentyields. Spectroscopy data for compounds 3 are in goodagreement with those previously reported.dd 30 g (0.20 mol) of phthalimide to a 1 L stainless steel magnetic stirring autoclave.A composite catalyst of 700 ml of methanol and 1.5 g of lanthanum chloride and copper powder supported alumina was used to seal the reaction vessel.After the air in the autoclave was replaced with nitrogen, the stirring was started to increase.When the temperature was raised to 250 C, the gauge pressure was 13.2 MPa. At this point, hydrogen is introduced.And pressurize to the pressure inside the kettle to 15Mpa. Insulation and pressure retention reaction for 30 hours, after the end of the heat preservation, Close the hydrogen inlet valve to cool to 10 C, After replacing the gas in the kettle with nitrogen, the liquid reaction solution was poured out. Filter, filter out the catalyst, The filtrate was transferred to a rotary evaporator.The methanol was distilled at atmospheric pressure, and after distilling off 600 ml of the distillate, the distillation was stopped. Cool to room temperature, A large amount of white granule crystals were precipitated, filtered through a Buchner funnel, and the filtrate and the distillate were combined.The filter cake was washed with 50 ml of water.The filter cake is dried to obtain 28.8 g of pure white crystalline powder, and the melting range is 138.8 C -140.3 C.The content of the liquid chromatographic analysis was 98.87%. The selectivity of the reaction is 93.05%, based on phthalimide.The yield was 94.11%.Cis-8-azabicyclo[4, 3, 0]nonane To a slurry of lithium aluminium hydride (17.1 g) in dry diethyl ether (375 ml) under a nitrogen atmosphere, Under a nitrogen atmosphere, the temperature was controlled at 20 to 30 C. 300 mL of a three-necked flask was successively added with 300 mL of tetrahydrofuran and 24.0 g of zinc chloride. After 1 hour, 8.2 g of potassium borohydride was added, and stirring was continued for 1 hour. Then, 7.8 g of