Cornforth reagent → 1-tert-Butyl 2-methyl 4-oxopyrrolidine-1,2-dicarboxylate

HRID 889054Notes

Reaction equation

HRID 889054 reaction equation
[CH3:1][O:2][C:3]([CH:5]1[CH2:9][CH:8]([OH:10])[CH2:7][N:6]1[C:11]([O:13][C:14]([CH3:17])([CH3:16])[CH3:15])=[O:12])=[O:4].[Cr](O[Cr]([O-])(=O)=O)([O-])(=O)=O.[NH+]1C=CC=CC=1.[NH+]1C=CC=CC=1>C(Cl)Cl>[CH3:1][O:2][C:3]([CH:5]1[CH2:9][C:8](=[O:10])[CH2:7][N:6]1[C:11]([O:13][C:14]([CH3:17])([CH3:16])[CH3:15])=[O:12])=[O:4]

Participants

4

Reactant 2

HCID 2724130Cornforth reagentHCID 51482991-Tert-butyl 2-methyl 4-hydroxypyrrolidine-1,2-dicarboxylate

Product 1

HCID 42518531-tert-Butyl 2-methyl 4-oxopyrrolidine-1,2-dicarboxylate

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of 4-hydroxy-pyrrolidine-1,2-dicarboxylic acid 1-tert-butyl ester 2-methyl ester (8 g, 32.65 mmol) in DCM (200 ml), pyridinium dichromate (24.55 g, 65.3 mmol) was added at 0° C. It was stirred at room temperature for overnight. Reaction mixture was filtered through celite pad and DCM layer was concentrated. Purification by column chromatography offered 4-oxo-pyrrolidine-1,2-dicarboxylic acid 1-tert-butyl ester 2-methyl ester as a white solid (6 g, 76%).

Workup

  1. customReaction mixture
  2. filtrationwas filtered through celite pad and DCM layer
  3. concentrationwas concentrated
  4. customPurification by column chromatography

Sources & evidence

ORD record
ord-b3102c1244354f1cab7b17600ea9ba29
Source dataset
uspto-grants-2012_08
Patent number
US08252797B2

Reaction notes

Loading…