Phenethyl bromide → 1-(Benzyloxycarbonyl)-2-(2-phenylethyl)pyrazolidin-3-one

HRID 727561Notes

Reaction equation

HRID 727561 reaction equation
[H-].[Na+].[CH2:3]([O:10][C:11]([N:13]1[CH2:17][CH2:16][C:15](=[O:18])[NH:14]1)=[O:12])[C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][CH:5]=1.Br[CH2:20][CH2:21][C:22]1[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=1>CN(C=O)C>[CH2:3]([O:10][C:11]([N:13]1[CH2:17][CH2:16][C:15](=[O:18])[N:14]1[CH2:20][CH2:21][C:22]1[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=1)=[O:12])[C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][CH:5]=1

Participants

5

Reactant 3

HCID 7666Phenethyl bromideHCID 24758Sodium hydrideHCID 19705542HCID 19705542, compound

Product 1

HCID 197054841-(Benzyloxycarbonyl)-2-(2-phenylethyl)pyrazolidin-3-oneYield 38%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

Sodium hydride (562 mg, 14.1 mmol, 60% mineral oil dispersion) is added to a solution of 1-(benzyloxycarbonyl)pyrazolidin-3-one (2.81 g, 12.8 mmol, prepared similarly to that described in J. Org. Chem. 1990, 55, 6037) and DMF (37 mL) at 0° C. The solution is stirred for 30 minutes and then (2-bromoethyl)benzene (1.90 mL, 13.9 mmol) is added. The solution is stirred at 0° C. for 1 hour and 16 hours at room temperature. Aqueous workup (EtOAc, brine, MgSO4) and purification by flash chromatography (2:1→1:1 hexane:EtOAc) gives 1.58 g (38%) of the title compound as an oil.

Workup

  1. customprepared similarly to
  2. customat 0° C
  3. stirringThe solution is stirred at 0° C. for 1 hour and 16 hours at room temperature
  4. customAqueous workup (EtOAc, brine, MgSO4) and purification by flash chromatography (2:1→1:1 hexane:EtOAc)

Sources & evidence

ORD record
ord-6a8c80fdc9df490fb6364cd5bd16eef8
Source dataset
uspto-grants-1998_01
Patent number
US05712300

Reaction notes

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