Water → HCID 18753678, compound

HRID 1838445Notes

Reaction equation

HRID 1838445 reaction equation
C(=O)([O-])[O-].[K+].[K+].[CH:7]1([NH2:10])[CH2:9][CH2:8]1.Br[CH:12]1[CH2:17][CH2:16][O:15][C:13]1=[O:14].O>C(#N)C>[CH:7]1([NH:10][CH:12]2[CH2:17][CH2:16][O:15][C:13]2=[O:14])[CH2:9][CH2:8]1

Participants

6

Reactant 4

HCID 962WaterHCID 11430Potassium CarbonateHCID 69828CyclopropylamineHCID 954632(3H)-Furanone, 3-bromodihydro-

Product 1

HCID 18753678HCID 18753678, compoundYield 73%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

After potassium carbonate (18.24 g, 132.0 mmol) was added to a solution of cyclopropylamine (5.50 ml, 80.0 mmol) and (±)-α-bromo-γ-butyrolactone (3.32 ml, 42.0 mmol) in acetonitrile (80 ml), the mixture was stirred at room temperature for 8 hours. To the reaction mixture, water was added and then this was extracted with ethyl acetate. The organic layer was washed with water, dried over anhydrous sodium sulfate and concentrated under reduced pressure. The residue was purified by chromatography on a silica gel column using hexane/ethyl acetate=1/1 as the eluant to give (±)-α-cyclopropylamino-γ-butyrolactone (4.10 g, yield 73%) as a yellow oil.

Workup

  1. extractionthis was extracted with ethyl acetate
  2. washThe organic layer was washed with water
  3. dry with materialdried over anhydrous sodium sulfate
  4. concentrationconcentrated under reduced pressure
  5. customThe residue was purified by chromatography on a silica gel column

Sources & evidence

ORD record
ord-c14e873eb3dc44c1b88e341e14484566
Source dataset
uspto-grants-2004_01
Patent number
US06673804B1

Reaction notes

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