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

HRID 1689876Notes

Reaction equation

HRID 1689876 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=O)C.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

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

Workup

  1. stirringThe reaction mixture was stirred at room temperature overnight
  2. washwashed with brine
  3. dry with materialdried (MgSO4)
  4. customthe solvent was removed in vacuo
  5. customThe resulting residue was purified

Sources & evidence

ORD record
ord-11cda931fa3949a883532e4b1cc927ac
Source dataset
uspto-grants-2012_04
Patent number
US08153629B2

Reaction notes

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