Potassium Carbonate → HCID 178516223, compound

HRID 415982Notes

Reaction equation

HRID 415982 reaction equation
[O:1]=[C:2]1[CH2:6][CH2:5][CH2:4][N:3]1[C@@H:7]1[CH2:12][CH2:11][C@H:10]([O:13]C(=O)C2C=CC([N+]([O-])=O)=CC=2)[CH2:9][CH2:8]1.C(=O)([O-])[O-].[K+].[K+]>CO.O>[OH:13][C@@H:10]1[CH2:9][CH2:8][C@H:7]([N:3]2[CH2:4][CH2:5][CH2:6][C:2]2=[O:1])[CH2:12][CH2:11]1

Participants

5

Reactant 2

HCID 11430Potassium CarbonateHCID 178525740HCID 178525740, compound

Product 1

HCID 178516223HCID 178516223, compoundYield 83%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 962WaterSolvent

Procedure

Dissolve cis-4-nitro-benzoic acid 4-(2-oxo-pyrrolidin-1-yl)-cyclohexyl ester (87.9 g, 264 mmol) in methanol (1.35 L) and water (150 mL) and treat with potassium carbonate (109.5 g, 800 mmol). Stir at room temperature overnight to give a white precipitate. Evaporate to dryness. Remove excess water by mixing with ethanol and concentrating to dryness under vacuum. Repeat this procedure. Stir in tetrahydrofuran (1 L) for 1 hour then filter. Evaporate the filtrate to an oil and crystallize from diethyl ether (100 mL) to afford 40 g (83%) of the title compound.

Workup

  1. customto give a white precipitate
  2. customEvaporate to dryness
  3. additionRemove excess water by mixing with ethanol
  4. concentrationconcentrating to dryness under vacuum
  5. stirringStir in tetrahydrofuran (1 L) for 1 hour
  6. filtrationthen filter
  7. customEvaporate the filtrate to an oil
  8. customcrystallize from diethyl ether (100 mL)

Sources & evidence

ORD record
ord-f9553b4d397846a2a3c8fa93a4628bcd
Source dataset
uspto-grants-2012_01
Patent number
US08088776B2

Reaction notes

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