methyl 1-benzyl-4-hydroxypyrrolidine-2-carboxylate

Conditions: temp:0.00; pressure:0.00; stir:

Conditions: temp:0.00; pressure:0.00; stir:

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

Procedure: A solution of 1-benzyl-4-hydroxy-pyrrolidine-2-carboxylic acid methyl ester (12.13 g, 49.5 mmol) in 250 mL of DCM cooled at 0° C. was treated with trichloroisocyanuric acid (11.48 g, 49.5 mmol) and TEMPO (770 mg, 4.95 mmol), and then the reaction mixture was stirred at 0° C. for 1 h. The mixture was diluted with DCM and washed with saturated aqueous NaHCO3, 1 M HCl, and brine. The organic layer was dried over Na2SO4 and concentrated to afford the product 1-benzyl-4-oxo-pyrrolidine-2-carboxylic acid methyl ester 11.5 g (96%) as a colorless oil. MS m/e=234.3 [M+H]+. washed with saturated aqueous NaHCO3, 1 M HCl, and brine The organic layer was dried over Na2SO4 concentrated

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

Procedure: A solution of a corresponding 1-benzyl-4-hydroxy-pyrrolidine-2-carboxylic acid methyl ester in DCM, cooled at 0° C. is treated with trichloroisocyanuric acid and TEMPO, and then the reaction mixture is stirred at 0° C. for about 1 h. The mixture is diluted with DCM and washed with NaHCO3, HCl, and brine. The organic layer is dried and concentrated to afford the product 1-benzyl-4-oxo-pyrrolidine-2-carboxylic acid methyl ester (25) washed with NaHCO3, HCl, and brine The organic layer is dried concentrated

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

Procedure: A solution of a corresponding 1-benzyl-4-hydroxy-pyrrolidine-2-carboxylic acid methyl ester in DCM, cooled at 0° C. is treated with trichloroisocyanuric acid and TEMPO, and then the reaction mixture is stirred at 0° C. for about 1 h. The mixture is diluted with DCM and washed with NaHCO3, HCl, and brine. The organic layer is dried and concentrated to afford the product 1-benzyl-4-oxo-pyrrolidine-2-carboxylic acid methyl ester (25) washed with NaHCO3, HCl, and brine The organic layer is dried concentrated

Conditions: temp:0.00; pressure:0.00; stir:

Conditions: temp:0.00; pressure:0.00; stir:

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

Procedure: A solution of 1-benzyl-4-hydroxy-pyrrolidine-2-carboxylic acid methyl ester (12.13 g, 49.5 mmol) in 250 mL of DCM cooled at 0° C. was treated with trichloroisocyanuric acid (11.48 g, 49.5 mmol) and TEMPO (770 mg, 4.95 mmol), and then the reaction mixture was stirred at 0° C. for 1 h. The mixture was diluted with DCM and washed with saturated aqueous NaHCO3, 1 M HCl, and brine. The organic layer was dried over Na2SO4 and concentrated to afford the product 1-benzyl-4-oxo-pyrrolidine-2-carboxylic acid methyl ester 11.5 g (96%) as a colorless oil. MS m/e=234.3 [M+H]+. washed with saturated aqueous NaHCO3, 1 M HCl, and brine The organic layer was dried over Na2SO4 concentrated

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

Procedure: A solution of a corresponding 1-benzyl-4-hydroxy-pyrrolidine-2-carboxylic acid methyl ester in DCM, cooled at 0° C. is treated with trichloroisocyanuric acid and TEMPO, and then the reaction mixture is stirred at 0° C. for about 1 h. The mixture is diluted with DCM and washed with NaHCO3, HCl, and brine. The organic layer is dried and concentrated to afford the product 1-benzyl-4-oxo-pyrrolidine-2-carboxylic acid methyl ester (25) washed with NaHCO3, HCl, and brine The organic layer is dried concentrated