1,4-Dibromobutane → 3-(4-Bromobutyl)-1-(phenylmethyl)-2-pyrrolidinone

HRID 1097728

Reaction equation

HRID 1097728 reaction equation
[C:1]1([CH2:7][N:8]2[CH2:12][CH2:11][CH2:10][C:9]2=[O:13])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[Br:14][CH2:15][CH2:16][CH2:17][CH2:18]Br.C1(CN2CCC3(CCCC3)C2=O)C=CC=CC=1>C1COCC1>[Br:14][CH2:15][CH2:16][CH2:17][CH2:18][CH:10]1[CH2:11][CH2:12][N:8]([CH2:7][C:1]2[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=2)[C:9]1=[O:13]

Participants

5

Reactant 3

HCID 80561,4-DibromobutaneHCID 791761-Benzyl-3-pyrrolidoneHCID 157074382-(Phenylmethyl)-2-azaspiro[4.4]nonan-1-one

Product 1

HCID 593958573-(4-Bromobutyl)-1-(phenylmethyl)-2-pyrrolidinone

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 1-(phenylmethyl)-2-pyrrolidinone (0.47 g, 2.7 mmol) in THF (10 ml) at −78° C. was added lithium hexamethyldisilylazine (2.8 ml, 2.7 mmol, 1M solution) over 5 min. After 15 min 1,4-dibromobutane (0.32 ml, 2.7 mmol) was added and the solution allowed to attain ambient temperature over 2 h then stirred for a further 18 h. The solution was separated between ethyl acetate and water and the organics isolated, dried and concentrated. Chromatography over silica (20 g SPE) eluting with cyclohexane then DCM and finally ether provided a clear oil which was a 1:1 mixture of the title compound and 2-(phenylmethyl)-2-azaspiro[4.4]nonan-1-one (0.17 g). This was used in the next step without further purification.

Workup

  1. customThe solution was separated between ethyl acetate and water
  2. customthe organics isolated, dried
  3. concentrationconcentrated
  4. washChromatography over silica (20 g SPE) eluting with cyclohexane
  5. customDCM and finally ether provided a clear oil which

Sources & evidence

ORD record
ord-d7f2e482a58640648abc361619115a0f
Source dataset
uspto-grants-2012_03
Patent number
US08143264B2

Linked notes

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