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

HRID 490579Notes

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 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)

Workup

washwashed with NaHCO3, HCl, and brine
customThe organic layer is dried
concentrationconcentrated

Sources & evidence

ORD record: ord-312d54bb810042adaecc478933655661
Source dataset: uspto-grants-2009_05
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07528136B2

Reaction notes

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