1-Acetoxy-2-bromoethane → 4-(2-Acetoxy-ethyl)-3-oxo-piperazine-1-carboxylic acid benzyl ester

HRID 2365193Notes

Reaction equation

HRID 2365193 reaction equation
[C:1]([N:11]1[CH2:16][CH2:15][NH:14][C:13](=[O:17])[CH2:12]1)([O:3][CH2:4][C:5]1[CH:10]=[CH:9][CH:8]=[CH:7][CH:6]=1)=[O:2].[H-].[Na+].Br[CH2:21][CH2:22][O:23][C:24](=[O:26])[CH3:25]>CN(C)C=O.C(OCC)(=O)C>[CH2:4]([O:3][C:1]([N:11]1[CH2:16][CH2:15][N:14]([CH2:21][CH2:22][O:23][C:24](=[O:26])[CH3:25])[C:13](=[O:17])[CH2:12]1)=[O:2])[C:5]1[CH:6]=[CH:7][CH:8]=[CH:9][CH:10]=1

Participants

6

Reactant 3

HCID 135641-Acetoxy-2-bromoethaneHCID 24758Sodium hydrideHCID 736777Benzyl 3-oxopiperazine-1-carboxylate

Product 1

HCID 574203464-(2-Acetoxy-ethyl)-3-oxo-piperazine-1-carboxylic acid benzyl ester

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Procedure

To 4-Cbz-piperazin-2-one (1.95 g) in N,N-dimethylformamide (5 mL) at 0° C. was added sodium hydride (60% dispersion in mineral oil, 660 mg) in several aliquots. After stirring for 1 hour, 2-bromoethylacetate (1.38 ml) was added. After stirring overnight at room temperature, the mixture was diluted with ethyl acetate, washed with brine, dried (MgSO4) and the solvent removed in vacuo. The residue was purified using flash chromatography to yield 4-(2-acetoxy-ethyl)-3-oxo-piperazine-1-carboxylic acid benzyl ester (925 mg).

Workup

  1. stirringAfter stirring overnight at room temperature
  2. washwashed with brine
  3. dry with materialdried (MgSO4)
  4. customthe solvent removed in vacuo
  5. customThe residue was purified

Sources & evidence

ORD record
ord-03ba2ee4fc64419c800d32837e486b87
Source dataset
uspto-grants-2014_04
Patent number
US08697693B2

Reaction notes

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