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Trifluoroacetic acid → 2-Oxa-7-azaspiro[3.5]nonane

HRID 2213014
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 2213014
FC(F)(F)C(O)=O.[CH2:8]1[C:11]2([CH2:16][CH2:15][N:14](C(OC(C)(C)C)=O)[CH2:13][CH2:12]2)[CH2:10][O:9]1.C(=O)([O-])O.[Na+]>ClCCl>[CH2:8]1[C:11]2([CH2:16][CH2:15][NH:14][CH2:13][CH2:12]2)[CH2:10][O:9]1
KomponentenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion

Komponenten

5

Edukt 3

HCID 6422Trifluoroacetic acidHCID 516892Sodium BicarbonateHCID 219552107-Boc-2-oxa-7-azaspiro[3.5]nonane

Produkt 1

HCID 219552842-Oxa-7-azaspiro[3.5]nonaneAusbeute 17 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6344DichloromethaneLösungsmittel2×

Versuchsvorschrift

Trifluoroacetic acid (5 mL) was added to a solution of 1,1-dimethylethyl 2-oxa-7-azaspiro[3.5]nonane-7-carboxylate (Description 69, 80 mg, 0.625 mmol) in dichloromethane (15 mL) and the mixture was stirred at room temperature for 3 hours. Saturated aqueous sodium hydrogen carbonate (3 mL) and dichloromethane (5 mL) were added and the layers were separated. The aqueous layer was extracted with dichloromethane (3×3 mL) and the combined organic fractions were poured onto an SCX cartridge (Varian Bond Elut™; 10 mL/500 mg). The cartridge was washed with methanol (4×2 mL), then eluted with methanolic ammonia (2M, 2×2 mL). The solvent was evaporated under reduced pressure to give the title compound as a colorless solid (8 mg, 17%). m/z (ES+) 128 (M+1).

Aufarbeitung

  1. customthe layers were separated
  2. extractionThe aqueous layer was extracted with dichloromethane (3×3 mL)
  3. additionthe combined organic fractions were poured onto an SCX cartridge (Varian Bond Elut™; 10 mL/500 mg)
  4. washThe cartridge was washed with methanol (4×2 mL)
  5. washeluted with methanolic ammonia (2M, 2×2 mL)
  6. customThe solvent was evaporated under reduced pressure

Quellen und Nachweise

ORD-Eintrag
ord-1314d738a66749bb93084e54da55d6f0
Quelldatensatz
uspto-grants-2006_09
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US07105507B2

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