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

HRID 265342Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 265342
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

Komponenten

7

Edukt 4

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

Produkt 1

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

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 6212ChloroformLösungsmittelHCID 6344DichloromethaneLösungsmittel

Versuchsvorschrift

To a stirred solution of 1-t-butyloxycarbonyl-4-(2-methyl-phenyl)-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.

Aufarbeitung

  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

Quellen und Nachweise

ORD-Eintrag
ord-7f284ae7bfd24bbba8d88f4533189565
Quelldatensatz
uspto-grants-1997_07
Patentnummer
US05648352

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