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Trifluoroacetic acid → 7-(3-Isopropoxy-4-nitrophenyl)-1,7-diazaspiro[4.4]nonane

HRID 518861
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 518861
FC(F)(F)C(O)=O.[N+:8]([C:11]1[CH:16]=[CH:15][C:14]([N:17]2[CH2:32][CH2:31][C:19]3([N:23](C(OC(C)(C)C)=O)[CH2:22][CH2:21][CH2:20]3)[CH2:18]2)=[CH:13][C:12]=1[O:33][CH:34]([CH3:36])[CH3:35])([O-:10])=[O:9].C(=O)([O-])[O-].[K+].[K+]>ClCCl>[N+:8]([C:11]1[CH:16]=[CH:15][C:14]([N:17]2[CH2:32][CH2:31][C:19]3([NH:23][CH2:22][CH2:21][CH2:20]3)[CH2:18]2)=[CH:13][C:12]=1[O:33][CH:34]([CH3:36])[CH3:35])([O-:10])=[O:9]
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Komponenten

5

Edukt 3

HCID 6422Trifluoroacetic acid2×HCID 11430Potassium CarbonateHCID 86698010Tert-butyl 7-(3-isopropoxy-4-nitrophenyl)-1,7-diazaspiro[4.4]nonane-1-carboxylate

Produkt 1

HCID 866980147-(3-Isopropoxy-4-nitrophenyl)-1,7-diazaspiro[4.4]nonaneAusbeute 97,8 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6344
Dichloromethane
Lösungsmittel

Versuchsvorschrift

0.33 ml of trifluoroacetic acid is added to a solution of 300 mg of 2-methylpropan-2-yl 7-[4-nitro-3-(propan-2-yloxy)phenyl]-1,7-diazaspiro[4.4]nonane-1-carboxylate in 30 ml of dichloromethane. The mixture is stirred at ambient temperature for 15 hours and then 3 ml of trifluoroacetic acid are again added. After stirring for 15 hours, the reaction mixture is run into 50 ml of a saturated potassium carbonate solution. The aqueous phase is extracted three times with 50 ml of dichloromethane. The organic phases are combined, dried over anhydrous magnesium sulfate, filtered and then concentrated to dryness under reduced pressure, so as to give a yellow oil. The residue is purified by chromatography on silica gel, elution being carried out with dichloromethane/methanol (100/0 to 95/5), so as to obtain 221 mg of 7-[4-nitro-3-(propan-2-yloxy)phenyl]-1,7-diazaspiro[4.4]nonane in the form of a yellow solid.

Aufarbeitung

  1. stirringAfter stirring for 15 hours
  2. extractionThe aqueous phase is extracted three times with 50 ml of dichloromethane
  3. dry with materialdried over anhydrous magnesium sulfate
  4. filtrationfiltered
  5. concentrationconcentrated to dryness under reduced pressure
  6. customso as to give a yellow oil
  7. customThe residue is purified by chromatography on silica gel, elution

Quellen und Nachweise

ORD-Eintrag
ord-4fd56fc34261438f8a7b983376fce421
Quelldatensatz
uspto-grants-2015_08
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US09115140B2

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