Benzyl Bromide → 3-Benzyl-1-cyclohexylpyrrolidin-2-one

HRID 1161778Notes

Reaction equation

HRID 1161778 reaction equation
[CH:1]1([N:7]2[CH2:11][CH2:10][CH2:9][C:8]2=[O:12])[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1.[Li+].CC([N-]C(C)C)C.[CH2:21](Br)[C:22]1[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=1>C1COCC1>[CH2:21]([CH:9]1[CH2:10][CH2:11][N:7]([CH:1]2[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6]2)[C:8]1=[O:12])[C:22]1[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=1

Participants

5

Reactant 3

HCID 7498Benzyl BromideHCID 81278N-Cyclohexyl-2-pyrrolidoneHCID 2724682Lithium diisopropylamide

Product 1

HCID 116733143-Benzyl-1-cyclohexylpyrrolidin-2-oneYield 70%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

Place 1-cyclohexyl-pyrrolidin-2-one (400 mg, 2.4 mmol) in THF (30 mL) and cool to −78° C. Slowly add LDA (2.0 M, 2.4 mL, 4.8 mmol) and stir for 15 minutes. Add benzyl bromide (1.23 g, 7.2 mmol) and stir for 3 hours. Quench with ammonium chloride and extract with dichloromethane. Dry over sodium sulfate, filter, and concentrate. Purify by silica gel (20-50% ethyl acetate in hexanes) to afford 432 mg (70%) of the title compound. Mass spectrum (apci) m/z=258.2 (M+H).

Workup

  1. customQuench with ammonium chloride
  2. extractionextract with dichloromethane
  3. dry with materialDry over sodium sulfate
  4. filtrationfilter
  5. concentrationconcentrate
  6. customPurify by silica gel (20-50% ethyl acetate in hexanes)

Sources & evidence

ORD record
ord-8003b4837fe14b74a8a40c2e56c4f30b
Source dataset
uspto-grants-2010_10
Patent number
US07820659B2

Reaction notes

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