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Hydrochloric Acid → 8-(2-Hydroxy-pyridin-3-yl)-2-(4-trifluoromethoxy-phenyl)-2,8-diaza-spiro[4.5]decan-1-one

HRID 1039010
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Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 1039010
C[O:2][C:3]1[C:8]([N:9]2[CH2:30][CH2:29][C:12]3([C:16](=[O:17])[N:15]([C:18]4[CH:23]=[CH:22][C:21]([O:24][C:25]([F:28])([F:27])[F:26])=[CH:20][CH:19]=4)[CH2:14][CH2:13]3)[CH2:11][CH2:10]2)=[CH:7][CH:6]=[CH:5][N:4]=1.[Na+].[I-].C[Si](Cl)(C)C.Cl.S(=O)(O)[O-].[Na+]>C(#N)C.[Cl-].[Na+].O.CCOC(C)=O>[OH:2][C:3]1[C:8]([N:9]2[CH2:10][CH2:11][C:12]3([C:16](=[O:17])[N:15]([C:18]4[CH:19]=[CH:20][C:21]([O:24][C:25]([F:27])([F:28])[F:26])=[CH:22][CH:23]=4)[CH2:14][CH2:13]3)[CH2:29][CH2:30]2)=[CH:7][CH:6]=[CH:5][N:4]=1
KomponentenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion

Komponenten

9

Edukt 5

HCID 313Hydrochloric AcidHCID 5238Sodium IodideHCID 6397ChlorotrimethylsilaneHCID 23665763Sodium BisulfiteHCID 56655687HCID 56655687, Verbindung

Produkt 1

HCID 1785172998-(2-Hydroxy-pyridin-3-yl)-2-(4-trifluoromethoxy-phenyl)-2,8-diaza-spiro[4.5]decan-1-one
Ausbeute 65 %

Reagenzien, Katalysatoren, Lösungsmittel 3

HCID 6342AcetonitrileLösungsmittelHCID 8857Ethyl AcetateLösungsmittelHCID 57417360Sodium chloride; waterLösungsmittel

Versuchsvorschrift

To a solution of 8-(2-methoxy-pyridin-3-yl)-2-(4-trifluoromethoxy-phenyl)-2,8-diaza-spiro[4.5]decan-1-one (described in example 9, 40 mg, 0.095 mmol) in acetonitrile (2 mL) at 0° C. was added NaI (28.5 mg, 0.19 mmol). TMSCl (24 uL, 0.19 mmol) was added, and the mixture was stirred and allowed to warm to rt over overnight. 1N Hydrochloric acid (1 mL), 38% aqueous sodium bisulfite solution (0.5 mL), brine and EtOAc (10 mL) were added, and the mixture was stirred for 30 min. The phases were separated, and the aqueous phase was extracted with additional EtOAc. The combined organic phases were washed with sat. NaHCO3, brine, dried (Na2SO4), filtered and evaporated under reduced pressure to yield the title compound as a light green solid (25 mg, 65%). MS (ESI): 408.3 (MH+).

Aufarbeitung

  1. stirringthe mixture was stirred for 30 min
  2. customThe phases were separated
  3. extractionthe aqueous phase was extracted with additional EtOAc
  4. washThe combined organic phases were washed with sat. NaHCO3, brine
  5. dry with materialdried (Na2SO4)
  6. filtrationfiltered
  7. customevaporated under reduced pressure

Quellen und Nachweise

ORD-Eintrag
ord-e031abb4cb9a4299aac34595feaa2236
Quelldatensatz
uspto-grants-2013_10
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US08552024B2

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