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

HRID 888939Notes

Reaction equation

HRID 888939 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-c2aa6750dbe84127b70a21a06e2c1d9f
Source dataset
uspto-grants-2012_08
Patent number
US08252792B2

Reaction notes

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