Water → N-isobutyl-3-bromopyrrolidine-2-one

HRID 1953166Notes

Reaction equation

HRID 1953166 reaction equation
[OH-].[Na+].[CH2:3]([NH2:7])[CH:4]([CH3:6])[CH3:5].[Br:8][CH:9]([CH2:13][CH2:14]Cl)[C:10](Cl)=[O:11].O>C([N+](CCCC)(CCCC)CCCC)CCC.S([O-])(O)(=O)=O.ClCCl>[CH2:3]([N:7]1[CH2:14][CH2:13][CH:9]([Br:8])[C:10]1=[O:11])[CH:4]([CH3:6])[CH3:5]

Participants

7

Reactant 4

HCID 962WaterHCID 6558IsobutylamineHCID 14798Sodium HydroxideHCID 100821792-Bromo-4-chlorobutanoyl chloride

Product 1

HCID 23303156N-isobutyl-3-bromopyrrolidine-2-oneYield 0.1%

Reagents, catalysts & solvents 2

HCID 94433Tetrabutylammonium hydrogen sulfateCatalystHCID 6344DichloromethaneSolvent2×

Procedure

In a 1.5-liter 4-necked flask, equipped with a stirrer, reflux condenser, thermometer and argon inlet, 54.4 g NaOH pearls (1.36 mol) and 9.26 g tetrabutylammonium-hydrogensulfate (27.3 mmol) were suspended at room temperature under argon in 500 ml dichloromethane. To this suspension 36.6 g isobutylamine (500 mol) were added. Under stirring 100.0 g 2-bromo-4-chlorobutyric acid chloride (400 mol, product of Example 1) in 100 ml dichloromethane were added in 10 min. After the first three minutes of addition reflux of the mixture was reached and maintained during the addition. Reflux of the mixture was continued for 2.0 h. After the first 10 minutes, the initially yellowish suspension turned purple, then gradually faded into gray. After completed reflux, the mixture was allowed to cool to room temperature during 15 min., a mixture of 50 g ice in 250 ml deionized water was added under stirring during 1 min., and the phases were separated. The organic phase was first washed with a solution of 60 g ammonium chloride in 300 ml deionized water, then with 300 ml deionized water, and finally evaporated to yield 84.3 g of N-isobutyl-3-bromopyrrolidine-2-one as a dark oil.

Workup

  1. customIn a 1.5-liter 4-necked flask, equipped with a stirrer
  2. temperaturereflux condenser
  3. additionwere added in 10 min
  4. additionAfter the first three minutes of addition
  5. temperaturereflux of the mixture
  6. temperaturemaintained during the addition
  7. temperatureReflux of the mixture
  8. customAfter the first 10 minutes
  9. temperatureAfter completed reflux
  10. additionwas added
  11. customthe phases were separated
  12. washThe organic phase was first washed with a solution of 60 g ammonium chloride in 300 ml
  13. customfinally evaporated

Sources & evidence

ORD record
ord-95887ecf20f643b4bd9d9cb3c42f4fb6
Source dataset
uspto-grants-2000_09
Patent number
US06114541

Reaction notes

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