Benzyl Bromide → 2-Pyrrolidinone, 5-(heptyloxy)-1-(phenylmethyl)-, (+-)-

HRID 1639041Notes

Reaction equation

HRID 1639041 reaction equation
[CH2:1]([O:8][CH:9]1[NH:13][C:12](=[O:14])[CH2:11][CH2:10]1)[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH3:7].[OH-].[K+].[CH2:17](Br)[C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1>[Br-].C([N+](CCCC)(CCCC)CCCC)CCC.O1CCCC1>[CH2:17]([N:13]1[CH:9]([O:8][CH2:1][CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH3:7])[CH2:10][CH2:11][C:12]1=[O:14])[C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1

Participants

6

Reactant 3

HCID 7498Benzyl BromideHCID 14797Potassium HydroxideHCID 156965645-(n-Heptyloxy)-pyrrolidin-2-one

Product 1

HCID 30779642-Pyrrolidinone, 5-(heptyloxy)-1-(phenylmethyl)-, (+-)-Yield 78.2%

Reagents, catalysts & solvents 2

HCID 74236Tetrabutylammonium BromideCatalystHCID 8028TetrahydrofuranSolvent2×

Procedure

To a mixture of 4 g of 5-(n-heptyloxy)-pyrrolidin-2-one, 1.68 g of potassium hydroxide hydrated to 85% and 0.4 g of tetra-n-butylammonium bromide in 55 cm3 of tetrahydrofuran, there is added a solution of 3.43 g of benzyl bromide in 20 cm3 of tetrahydrofuran, operating at 20° C. to 25° C. After agitating for 1 hour at ambient temperature, filtering, and evaporating the solvent to dryness under reduced pressure, the residue is chromatographed on silica (eluent: ethyl acetate--n-hexane, 1-2), and 4.54 g of the expected product is obtained.

Workup

  1. customoperating at 20° C. to 25° C
  2. filtrationfiltering
  3. customevaporating the solvent to dryness under reduced pressure
  4. customthe residue is chromatographed on silica (eluent: ethyl acetate--n-hexane, 1-2)

Sources & evidence

ORD record
ord-408876085bf447b188c1e009e8744c64
Source dataset
uspto-grants-1989_11
Patent number
US04882350

Reaction notes

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