1-benzyl-pyrrolidine-2,5-dicarboxylic acid diethyl ester(HCl)

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

Procedure: To a suspension of lithium aluminum hydride 10.25 g) in tetrahydrofuran (550 ml) was added dropwise a solution of 1-benzyl-2,5-bis(ethoxycarbonyl)pyrrolidine (55 g) in tetrahydrofuran (100 ml). The reaction mixture was stirred for 30 minutes at 0° C., allowed to warm to room temperature and then stirred at the same temperature for 1 hour. And then water was added carefully until excess lithium aluminum hydride was decomposed. After the precipitate was filtered off, the filtrate was evaporated under reduced pressure to give crude 1-benzyl-2,5-bis(hydroxymethyl)pyrrolidine (38.52 g). to warm to room temperature stirred at the same temperature for 1 hour After the precipitate was filtered off the filtrate was evaporated under reduced pressure

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

Procedure: To a suspension of lithium aluminum hydride (10.25 g) in tetrahydrofuran (550 ml) was added dropwise a solution of 1-benzyl-2,5-bis(ethoxycarbonyl)pyrrolidine (55 g) in tetrahydrofuran (100 ml). The reaction mixture was stirred for 30 minutes at 0° C., allowed to warm to room temperature and then stirred at the same temperature for 1 hour. And then water was added carefully until excess lithium aluminum hydride was decomposed. After the precipitate was filtered off, the filtrate was evaporated under reduced pressure to give crude 1-benzyl-2,5-bis(hydroxymethyl)pyrrolidine (38.52 g). to warm to room temperature stirred at the same temperature for 1 hour After the precipitate was filtered off the filtrate was evaporated under reduced pressure

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

Procedure: A solution of Diethyl meso-2,5-dibromoadipate (50 g, 139 mmol) in benzene (150 mL) was heated to reflux. Then heating was discontinued and benzylamine (50 mL) was added under stirring in 1 h. At the end of the addition, the mixture was refluxed for 20 h. After cooling down, the hydrobromide salt was filtered off and washed with benzene, and the benzene solution was evaporated. The residue was distilled under reduced pressure (180-190° C./0.3 mmHg) to give a product (39.9 g, 94%) as a yellow oil. Then heating At the end of the addition the mixture was refluxed for 20 h After cooling down the hydrobromide salt was filtered off washed with benzene the benzene solution was evaporated The residue was distilled under reduced pressure (180-190° C./0.3 mmHg)

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

Procedure: To a suspension of lithium aluminum hydride 10.25 g) in tetrahydrofuran (550 ml) was added dropwise a solution of 1-benzyl-2,5-bis(ethoxycarbonyl)pyrrolidine (55 g) in tetrahydrofuran (100 ml). The reaction mixture was stirred for 30 minutes at 0° C., allowed to warm to room temperature and then stirred at the same temperature for 1 hour. And then water was added carefully until excess lithium aluminum hydride was decomposed. After the precipitate was filtered off, the filtrate was evaporated under reduced pressure to give crude 1-benzyl-2,5-bis(hydroxymethyl)pyrrolidine (38.52 g). to warm to room temperature stirred at the same temperature for 1 hour After the precipitate was filtered off the filtrate was evaporated under reduced pressure