Trichloroisocyanuric Acid → Benzyl-4-oxo-pyrrolidine-2-carboxylic acid methyl ester

HRID 490628Notes

Reaction equation

[CH3:1][O:2][C:3]([CH:5]1[CH2:9][CH:8]([OH:10])[CH2:7][N:6]1[CH2:11][C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1)=[O:4].ClN1C(=O)N(Cl)C(=O)N(Cl)C1=O.CC1(C)N([O])C(C)(C)CCC1>C(Cl)Cl>[CH3:1][O:2][C:3]([CH:5]1[CH2:9][C:8](=[O:10])[CH2:7][N:6]1[CH2:11][C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1)=[O:4]

Participants

Conditions

Temperature: 0 °C

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]+.

Workup

washwashed with saturated aqueous NaHCO3, 1 M HCl, and brine
dry with materialThe organic layer was dried over Na2SO4
concentrationconcentrated

Sources & evidence

ORD record: ord-47b5fdf8616e4563a511374b56860932
Source dataset: uspto-grants-2009_05
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07528136B2

Reaction notes

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