Isobutyl iodide → 3-(2-Methylpropyl)-1-(2-phenylethyl)-2-pyrrolidinone

HRID 727519Notes

Reaction equation

HRID 727519 reaction equation
[C:1]1([CH2:7][CH2:8][N:9]2[CH2:13][CH2:12][CH2:11][C:10]2=[O:14])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.C([N-]C(C)C)(C)C.[Li+].I[CH2:24][CH:25]([CH3:27])[CH3:26]>C1COCC1>[CH3:24][CH:25]([CH3:27])[CH2:26][CH:11]1[CH2:12][CH2:13][N:9]([CH2:8][CH2:7][C:1]2[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=2)[C:10]1=[O:14]

Participants

5

Reactant 3

HCID 10556Isobutyl iodideHCID 7469811-(2-Phenylethyl)pyrrolidin-2-oneHCID 2724682Lithium diisopropylamide

Product 1

HCID 197055603-(2-Methylpropyl)-1-(2-phenylethyl)-2-pyrrolidinoneYield 99.1%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
-78 °C

Procedure

A solution of 1-(2-phenylethyl)-2-pyrrolidinone (500 mg, 2.64 mmol) and THF (6 mL) is cooled to -78° C. Some precipitation occurred and 2 mL of THF is added. A solution of lithium diisopropylamide (LDA, 1.4 mL, 2.8 mmol, 2.0M in heptane/THF/ethylbenzene) is added and the mixture stirred at -78° C. for 40 minutes, giving a dark brown solution. To this solution is added 1-iodo-2-methylpropane (0.37 mL, 3.2 mmol). The solution is allowed to warm from -78° C. to 5° C. over 2.5 hours. After quenching with saturated aqueous ammonium chloride, aqueous workup (EtOAc, MgSO4) and purification by column chromatography (20% EtOAc/hexane) to give 642 mg (99%) of the title compound as a white solid (mp 69°-71° C.).

Workup

  1. customSome precipitation
  2. addition2 mL of THF is added
  3. customgiving a dark brown solution
  4. temperatureto warm from -78° C. to 5° C. over 2.5 hours
  5. customAfter quenching with saturated aqueous ammonium chloride, aqueous workup (EtOAc, MgSO4) and purification by column chromatography (20% EtOAc/hexane)

Sources & evidence

ORD record
ord-e7798fee0fd941e98f03b2599f561bf8
Source dataset
uspto-grants-1998_01
Patent number
US05712300

Reaction notes

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