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Benzophenone imine → 6-(1,4-dioxaspiro[4.5]decan-8-yl)-N-(diphenylmethylene)-5-methylpyridin-3-amine

HRID 1748536
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 1748536
Br[C:2]1[CH:3]=[C:4]([CH3:18])[C:5]([C:8]2[CH2:17][CH2:16][C:11]3([O:15][CH2:14][CH2:13][O:12]3)[CH2:10][CH:9]=2)=[N:6][CH:7]=1.[C:19](=[NH:32])([C:26]1[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=1)[C:20]1[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1.CC(C)([O-])C.[Na+]>C1(C)C=CC=CC=1.C([O-])(=O)C.[Pd+2].C([O-])(=O)C.C1(P(C2C=CC=CC=2)C2C=CC3C(=CC=CC=3)C=2C2C3C(=CC=CC=3)C=CC=2P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1>[O:15]1[C:11]2([CH2:16][CH2:17][CH:8]([C:5]3[N:6]=[CH:7][C:2]([N:32]=[C:19]([C:20]4[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=4)[C:26]4[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=4)=[CH:3][C:4]=3[CH3:18])[CH2:9][CH2:10]2)[O:12][CH2:13][CH2:14]1
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Komponenten

7

Edukt 3

HCID 136809Benzophenone imineHCID 23676156Sodium t-butoxideHCID 866924755-Bromo-2-(1,4-dioxaspiro[4.5]dec-7-en-8-yl)-3-methylpyridine

Produkt 1

HCID 866924886-(1,4-dioxaspiro[4.5]decan-8-yl)-N-(diphenylmethylene)-5-methylpyridin-3-amineAusbeute 93,6 %

Reagenzien, Katalysatoren, Lösungsmittel 3

HCID 167845
palladium(II) acetate
Katalysator
HCID 634876Binap, (A+-)-Katalysator
HCID 1140TolueneLösungsmittel

Versuchsvorschrift

A suspension of 5-bromo-2-(1,4-dioxaspiro[4.5]decan-7-en-8-yl)-3-methylpyridine (22.5 g) in Reference Example 105, benzophenone imine (13.9 g), palladium acetate (204 mg), (±)-2,2′-bis(diphenylphosphino)-1,1′-binaphthyl (567 mg) and sodium tert-butoxide (10.5 g) in toluene (150 ml) was stirred for 6 hours under heating to reflux. After completion of the reaction, the mixture was allowed to cool, ice water was added thereto, and the mixture was extracted with chloroform. The organic layer was dried over anhydrous sodium sulfate, and then the solvent was evaporated to give 6-(1,4-dioxaspiro[4.5]decan-8-yl)-N-(diphenylmethylene)-5-methylpyridin-3-amine (28 g) as a brown oil. MS (ESI) m/z: 411 (M+H)+.

Aufarbeitung

  1. temperatureunder heating to reflux
  2. customAfter completion of the reaction
  3. temperatureto cool
  4. extractionthe mixture was extracted with chloroform
  5. dry with materialThe organic layer was dried over anhydrous sodium sulfate
  6. customthe solvent was evaporated

Quellen und Nachweise

ORD-Eintrag
ord-d6cfad3138474c5794ace8faea48788e
Quelldatensatz
uspto-grants-2015_10
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US09150555B2

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