18-Crown-6 → HCID 22560293, compound

HRID 983405Notes

Reaction equation

HRID 983405 reaction equation
[CH2:1]([N:8]1[CH2:12][CH2:11][CH:10]([C:13](=[O:16])[CH2:14]Br)[C:9]1=[O:17])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C1OCCOCCOCCOCCOCCOC1.[F-:36].[K+]>C(#N)C>[CH2:1]([N:8]1[CH2:12][CH2:11][CH:10]([C:13](=[O:16])[CH2:14][F:36])[C:9]1=[O:17])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

5

Reactant 3

HCID 2855718-Crown-6HCID 522689Potassium FluorideHCID 22560353HCID 22560353, compound

Product 1

HCID 22560293HCID 22560293, compoundYield 29.5%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

To a solution of 1-benzyl-3-(2-bromoacetyl)pyrrolidin-2-one (2.2 g, 7.43 mmol, Example 14) in acetonitrile (25 mL) was added 18-crown-6 (0.980 g, 3.72 mmol) and potassium fluoride (spray dried) (2.16 g, 37.2 mmol). The reaction mixture was immersed in an oil bath at 80° C. After 1 hour, the mixture was cooled to room temperature and partitioned between water and ethyl acetate. The organic layer was dried over magnesium sulfate, filtered and concentrated. The crude residue was then purified by chromatography (99:1 dichloromethane/methanol then 98:2 dichloromethane/methanol) to afford the title compound (0.515 g): 1H NMR (CDCl3) δ 7.36-7.19 (m, 5H), 4.93 (m, 2H), 4.46 (m, 2H), 3.61 (m, 1H), 3.48 (m, 2H), 2.74 (m, 2H).

Workup

  1. customThe reaction mixture was immersed in an oil bath at 80° C
  2. custompartitioned between water and ethyl acetate
  3. dry with materialThe organic layer was dried over magnesium sulfate
  4. filtrationfiltered
  5. concentrationconcentrated
  6. customThe crude residue was then purified by chromatography (99:1 dichloromethane/methanol

Sources & evidence

ORD record
ord-7d1bd4c866fb4db9b7e9f1a030a95f8d
Source dataset
uspto-grants-2005_03
Patent number
US06864259B2

Reaction notes

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