2-Dimethylaminopyridine → 2-Benzyl 1-tert-butyl (2S)-5-oxopyrrolidine-1,2-dicarboxylate

HRID 604976Notes

Reaction equation

HRID 604976 reaction equation
[CH2:1]([O:8][C:9]([C@@H:11]1[CH2:15][CH2:14][C:13](=[O:16])[NH:12]1)=[O:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.CN(C1C=CC=CN=1)C.[C:26](=O)([O:32]C(C)(C)C)[O:27][C:28]([CH3:31])([CH3:30])[CH3:29]>ClCCl>[C:28]([O:27][C:26]([N:12]1[C:13](=[O:16])[CH2:14][CH2:15][C@H:11]1[C:9]([O:8][CH2:1][C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1)=[O:10])=[O:32])([CH3:31])([CH3:30])[CH3:29]

Participants

5

Reactant 3

HCID 218852-DimethylaminopyridineHCID 2381219Benzyl 5-oxoprolinateHCID 10219638Carbonic acid, bis(1,1-dimethylethyl) ester

Product 1

HCID 80274822-Benzyl 1-tert-butyl (2S)-5-oxopyrrolidine-1,2-dicarboxylate

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of 78.9 g of (S)-5-oxo-pyrrolidine-2-carboxylic acid benzyl ester in 400 mL of dichloromethane is added 2.20 g of dimethylaminopyridine and 78.54 g of di-tert-butyl carbonate at room temperature. The mixture is stirred for 4 hours at room temperature. The reaction mixture is then washed twice with 400 mL of 0.5 M sulphuric acid. The organic phase is separated and the solvent removed to give (S)-5-oxo-pyrrolidine-1,2-dicarboxylic acid 2-benzyl ester 1-tert-butyl ester as a semi-crystalline solid.

Workup

  1. washThe reaction mixture is then washed twice with 400 mL of 0.5 M sulphuric acid
  2. customThe organic phase is separated
  3. customthe solvent removed

Sources & evidence

ORD record
ord-afbf95d4e359488ba97c1e694571a489
Source dataset
uspto-grants-2011_03
Patent number
US07910774B2

Reaction notes

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