Hydrochloric Acid → 1-(4-Oxocyclohexyl)pyrrolidin-2-one

HRID 1896857Notes

Reaction equation

HRID 1896857 reaction equation
O1[C:5]2([CH2:10][CH2:9][CH:8]([N:11]3[CH2:15][CH2:14][CH2:13][C:12]3=[O:16])[CH2:7][CH2:6]2)[O:4]CC1.Cl>C(#N)C>[O:4]=[C:5]1[CH2:6][CH2:7][CH:8]([N:11]2[CH2:15][CH2:14][CH2:13][C:12]2=[O:16])[CH2:9][CH2:10]1

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 109002931-(1,4-Dioxaspiro[4.5]decan-8-yl)pyrrolidin-2-one

Product 1

HCID 585626831-(4-Oxocyclohexyl)pyrrolidin-2-oneYield 99.1%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

1-(1,4-dioxaspiro[4.5]decan-8-yl)pyrrolidin-2-one (143 mg, 0.64 mmol) from above step B, was dissolved in acetonitrile, treated with 6N HCl, and stirred at room temperature for 18 h. reaction mixture was concentrated in vacuo, treated with saturated NaHCO3 to pH 6. The solvents were removed under vacuum and the residue treated with saturated NaCl (2 mL) and extracted with 4:1 EtOAc/iPrOH (×4). The organic fractions were combined, filtered and evaporated to give 115 mg of 1-(4-oxocyclohexyl)pyrrolidin-2-one.

Workup

  1. customreaction mixture
  2. concentrationwas concentrated in vacuo
  3. additiontreated with saturated NaHCO3 to pH 6
  4. customThe solvents were removed under vacuum
  5. additionthe residue treated with saturated NaCl (2 mL)
  6. extractionextracted with 4:1 EtOAc/iPrOH (×4)
  7. filtrationfiltered
  8. customevaporated

Sources & evidence

ORD record
ord-a16d52273e634d048f2f8b178af029a3
Source dataset
uspto-grants-2013_08
Patent number
US08518969B2

Reaction notes

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