Ammonium Hydroxide → 3-(4-Methoxycyclohexyl)-pyrrolidin-2-one

HRID 1670833Notes

Reaction equation

HRID 1670833 reaction equation
[CH3:1][O:2][CH:3]1[CH2:8][CH2:7][CH:6]([CH:9]2[CH2:13][CH2:12][O:11][C:10]2=O)[CH2:5][CH2:4]1.[OH-].[NH4+:16]>C(O)C>[CH3:1][O:2][CH:3]1[CH2:8][CH2:7][CH:6]([CH:9]2[CH2:13][CH2:12][NH:16][C:10]2=[O:11])[CH2:5][CH2:4]1

Participants

4

Reactant 2

HCID 14923Ammonium HydroxideHCID 673560023-(4-Methoxycyclohexyl)-dihydro-furan-2-one

Product 1

HCID 673564923-(4-Methoxycyclohexyl)-pyrrolidin-2-one

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

Heat a mixture of 3-(4-methoxycyclohexyl)-dihydro-furan-2-one (0.91 g), ammonium hydroxide (20 mL) and ethanol (20 mL) at 230° C. in a sealed steel bottle for 12 hours. Cool the reaction and remove the solvent in vacuo. Partition the residue with ethyl acetate (100 mL) and HCl (1N, 60 mL). Dry the organic over sodium sulfate. After filtration and concentration, recrystallize with 1:3 ethyl acetate:hexane to afford 0.71 gram of the title compound.

Workup

  1. temperatureHeat
  2. temperatureCool
  3. customthe reaction
  4. customremove the solvent in vacuo
  5. customPartition the residue with ethyl acetate (100 mL) and HCl (1N, 60 mL)
  6. dry with materialDry the organic over sodium sulfate
  7. filtrationAfter filtration and concentration
  8. customrecrystallize with 1:3 ethyl acetate

Sources & evidence

ORD record
ord-59ef374852b84706b8aaff523165ce83
Source dataset
uspto-grants-2011_08
Patent number
US07994176B2

Reaction notes

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