N-bromobutanimide → Isohexane ethyl acetate

HRID 427471Notes

Reaction equation

HRID 427471 reaction equation
N1[CH:6]=[CH:5][C:4](N2C[CH2:10][CH:9]([O:12][Si](C(C)(C)C)(C)C)C2)=[CH:3][CH:2]=1.BrN1[C:25](=[O:26])[CH2:24]C[C:22]1=O>C(#N)C>[CH3:24][CH2:25][O:26][C:9]([CH3:10])=[O:12].[CH3:6][CH2:5][CH2:4][CH:3]([CH3:2])[CH3:22]

Participants

4

Reactant 2

HCID 67184N-bromobutanimideHCID 18357141HCID 18357141, compound

Product 1

HCID 21882781Isohexane ethyl acetate

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

1-(4-Pyridyl)-3-(t-butyldimethylsilyloxy)pyrrolidine (8.92 g, 32.1 mmol) was dissolved in acetonitrile (140 ml) and N-bromosuccinimide (6.00 g, 33.7 mmol) was added portionwise. After stirring overnight the solvent was removed under reduced pressure and the residue partitioned between dichloromethane and water. The organic layer was dried over sodium sulphate. After evaporation of the solvent, the residue was purified by column chromatography on silica gel, eluting sequentially with CH2Cl2; 5%MeOH CH2Cl2; 10%MeOH/CH2Cl2. Further purification by column chromatography on alumina, eluting sequentially with isohexane; 25%EtOAc/isohexane gave the product as a colourless oil.

Workup

  1. customwas removed under reduced pressure
  2. customthe residue partitioned between dichloromethane and water
  3. dry with materialThe organic layer was dried over sodium sulphate
  4. customAfter evaporation of the solvent
  5. customthe residue was purified by column chromatography on silica gel
  6. washeluting sequentially with CH2Cl2
  7. customFurther purification by column chromatography on alumina
  8. washeluting sequentially with isohexane

Sources & evidence

ORD record
ord-9660624133c44be7a8114fb63adbacab
Source dataset
uspto-grants-2001_11
Patent number
US06313127B1

Reaction notes

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