Trifluoroacetic acid → 1-((7,7-Dimethyl-2-oxo-bicyclo(2.2.1)heptan-1-yl)methanesulfonyl)-4-(2-methylphenyl)-3-piperazinone

HRID 2293576Notes

Reaction equation

HRID 2293576 reaction equation
C(OC([N:8]1[CH2:13][CH2:12][N:11]([C:14]2[CH:19]=[CH:18][CH:17]=[CH:16][C:15]=2[CH3:20])[C:10](=[O:21])[CH2:9]1)=O)(C)(C)C.C(O)(C(F)(F)F)=O.[CH3:29][C:30]1([CH3:43])[C:34]2([CH2:38][S:39](Cl)(=[O:41])=[O:40])[C:35]([CH2:37][CH:31]1[CH2:32][CH2:33]2)=[O:36].C(N(CC)CC)C>ClCCl.C(Cl)(Cl)Cl>[CH3:29][C:30]1([CH3:43])[CH:31]2[CH2:32][CH2:33][C:34]1([CH2:38][S:39]([N:8]1[CH2:13][CH2:12][N:11]([C:14]3[CH:19]=[CH:18][CH:17]=[CH:16][C:15]=3[CH3:20])[C:10](=[O:21])[CH2:9]1)(=[O:41])=[O:40])[C:35](=[O:36])[CH2:37]2

Participants

7

Reactant 4

HCID 6422Trifluoroacetic acidHCID 8471TriethylamineHCID 26579910-Camphorsulfonyl chlorideHCID 214763281,1-Dimethylethyl 4-(2-methylphenyl)-3-oxo-1-piperazinecarboxylate

Product 1

HCID 214763111-((7,7-Dimethyl-2-oxo-bicyclo(2.2.1)heptan-1-yl)methanesulfonyl)-4-(2-methylphenyl)-3-piperazinone

Reagents, catalysts & solvents 2

HCID 6212ChloroformSolventHCID 6344DichloromethaneSolvent

Procedure

To a stirred solution of 1-t-butyloxycarbonyl-4-(2-methylphenyl)-3-piperazinone (0.25 g; 0.86 mmol) in dichloromethane (3 mL) was added TFA (1 mL). After 1 hour the solvents were removed under reduced pressure and the residue was taken up into chloroform and evaporated several times to remove excess TFA. The residue was dissolved in chloroform (5 mL) and added to the stirred solution was 10-camphorsulfonyl chloride (376 mg; 1.50 mmol) and triethylamine (0.38 mL; 2.7 mmol). After 12 hours, the mixture was diluted with chloroform (25 mL) and extracted with 5% aqueous HCl (25 mL), water (25 mL), and aqueous NaHCO3 (25 mL). The organic phase was dried (MgSO4), filtered, and the solvent was removed under reduced pressure. The residue was purified by pressurized silica gel column chromatography using 2:1 hexane-ethyl acetate as eluant. The title compound was obtained as a white foam from ether-hexane.

Workup

  1. customAfter 1 hour the solvents were removed under reduced pressure
  2. customevaporated several times
  3. customto remove excess TFA
  4. dissolutionThe residue was dissolved in chloroform (5 mL)
  5. additionadded to the stirred solution
  6. extractionextracted with 5% aqueous HCl (25 mL), water (25 mL), and aqueous NaHCO3 (25 mL)
  7. dry with materialThe organic phase was dried (MgSO4)
  8. filtrationfiltered
  9. customthe solvent was removed under reduced pressure
  10. customThe residue was purified by pressurized silica gel column chromatography

Sources & evidence

ORD record
ord-9312d2e50ec7416ba9e0fcc776846f2d
Source dataset
uspto-grants-1997_11
Patent number
US05686454

Reaction notes

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