Trifluoroacetic acid → 3,3-Dimethyl-2-oxa-8-azaspiro[4.5]decan-1-one

HRID 2213027Notes

Reaction equation

HRID 2213027 reaction equation
FC(F)(F)C(O)=O.[CH3:8][C:9](=[CH2:29])[CH2:10][C:11]1([C:24]([O:26]CC)=[O:25])[CH2:16][CH2:15][N:14](C(OC(C)(C)C)=O)[CH2:13][CH2:12]1>ClCCl>[CH3:8][C:9]1([CH3:29])[CH2:10][C:11]2([CH2:16][CH2:15][NH:14][CH2:13][CH2:12]2)[C:24](=[O:26])[O:25]1

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 69559116HCID 69559116, compound

Product 1

HCID 219552143,3-Dimethyl-2-oxa-8-azaspiro[4.5]decan-1-oneYield 87.2%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Trifluoroacetic acid (50 mL) was added to a solution of 1-(1,1-dimethylethyl) 4-ethyl 4-(2-methyl-2-propenyl)-1,4-piperidinedicarboxylate (Description 89, 10.86 g, 35 mmol) in dichloromethane (10 mL) and the mixture was stirred at 50 C for 8 hours. The mixture was cooled and the solvent was evaporated under reduced pressure. Ether (50 mL) was added and the mixture was extracted with hydrochloric acid (1M, 3×50 mL). The combined aqueous fractions were washed with ether (2×50 mL), adjusted to pH 12 with aqueous sodium hydroxide (4M) and the mixture was extracted with ethyl acetate (6×50 mL). The combined organic fractions were dried (MgSO4) and the solvent was evaporated under reduced pressure. The residue was dissolved in ethanol (50 mL), cooled in ice and and ethereal hydrogen chloride (1M, 35 mL) was added slowly. The solvent was evaporated under reduced pressure, ethanol (75 mL) was added and the mixture was heated under reflux for 15 minutes. The mixture was cooled and the solid was collected and dried in vacuo to give the title compound as a colorless solid (5.59 g, 73%), m.p.>280° C. m/z (ES+) 184 (M+1).

Workup

  1. temperatureThe mixture was cooled
  2. customthe solvent was evaporated under reduced pressure
  3. additionEther (50 mL) was added
  4. extractionthe mixture was extracted with hydrochloric acid (1M, 3×50 mL)
  5. washThe combined aqueous fractions were washed with ether (2×50 mL)
  6. extractionthe mixture was extracted with ethyl acetate (6×50 mL)
  7. dry with materialThe combined organic fractions were dried (MgSO4)
  8. customthe solvent was evaporated under reduced pressure
  9. dissolutionThe residue was dissolved in ethanol (50 mL)
  10. temperaturecooled in ice
  11. additionethereal hydrogen chloride (1M, 35 mL) was added slowly
  12. customThe solvent was evaporated under reduced pressure, ethanol (75 mL)
  13. additionwas added
  14. temperaturethe mixture was heated
  15. temperatureunder reflux for 15 minutes
  16. temperatureThe mixture was cooled
  17. customthe solid was collected
  18. customdried in vacuo

Sources & evidence

ORD record
ord-139c00b6b04a44d7b93ee9ec6bae25fb
Source dataset
uspto-grants-2006_09
Patent number
US07105507B2

Reaction notes

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