1-(Phenylmethyl)-2,5-pyrrolidinedione → HCID 58504592, compound

HRID 2367229

Reaction equation

HRID 2367229 reaction equation
[C:1]1([CH2:7][N:8]2[C:12](=[O:13])[CH2:11][CH2:10][C:9]2=[O:14])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[CH:15]1([Mg]Br)[CH2:17][CH2:16]1>C1COCC1>[CH:15]1([C:12]2([OH:13])[N:8]([CH2:7][C:1]3[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=3)[C:9](=[O:14])[CH2:10][CH2:11]2)[CH2:17][CH2:16]1

Participants

4

Reactant 2

HCID 952411-(Phenylmethyl)-2,5-pyrrolidinedioneHCID 178418630HCID 178418630, compound

Product 1

HCID 58504592HCID 58504592, compoundYield 33%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
0 °C

Procedure

To 1-(phenylmethyl)-2,5-pyrrolidinedione (1 g, 5.29 mmol) in THF (50 mL) at −78° C. was added cyclopropylmagnesium bromide (42.3 mL, 21.1 mmol) dropwise. The reaction mixture was allowed to warm to 0° C. and stirred for an additional 2 hours. The reaction was quenched with a saturated aqueous solution of ammonium chloride and transferred to a separatory funnel. EtOAc was added, and the organic phase was separated. The aqueous layer was further extracted with EtOAc, and the combined organic layers were washed with brine, dried (MgSO4), filtered and concentrated. Flash chromatography on SiO2 (gradient: 100% hexanes to 80% EtOAc/hexanes) afforded the title compound (400 mg, 33%) as a yellow solid. LC-MS (ES) m/z=232 [M+H]+.

Workup

  1. customThe reaction was quenched with a saturated aqueous solution of ammonium chloride
  2. customtransferred to a separatory funnel
  3. additionEtOAc was added
  4. customthe organic phase was separated
  5. extractionThe aqueous layer was further extracted with EtOAc
  6. washthe combined organic layers were washed with brine
  7. dry with materialdried (MgSO4)
  8. filtrationfiltered
  9. concentrationconcentrated

Sources & evidence

ORD record
ord-ae820360a90240069134d3d173d5b4f2
Source dataset
uspto-grants-2014_04
Patent number
US08697685B2

Linked notes

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