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Formamide → (5R)-5-{(E)-2-(4-tert-butylphenyl)-2-[5-(dimethylamino)-6-methoxypyridin-2-yl]ethenyl}pyrrolidin-2-one

HRID 70649
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Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 70649
[CH:1]([NH2:3])=O.N[C:5]1[CH:6]=[CH:7][C:8](/[C:13](/[C:21]2[CH:26]=[CH:25][C:24]([C:27]([CH3:30])([CH3:29])[CH3:28])=[CH:23][CH:22]=2)=[CH:14]/[C@@H:15]2[NH:19]C(=O)C[CH2:16]2)=[N:9][C:10]=1OC.C(O[BH-](O[C:41](=[O:43])[CH3:42])OC(=O)C)(=O)C.[Na+].[C:45](=[O:48])(O)[O-].[Na+].[C:50](#N)C>>[C:27]([C:24]1[CH:25]=[CH:26][C:21](/[C:13](/[C:8]2[CH:7]=[CH:6][C:5]([N:3]([CH3:1])[CH3:50])=[C:10]([O:48][CH3:45])[N:9]=2)=[CH:14]\[C@@H:15]2[NH:19][C:41](=[O:43])[CH2:42][CH2:16]2)=[CH:22][CH:23]=1)([CH3:28])([CH3:29])[CH3:30]
KomponentenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion

Komponenten

6

Edukt 5

HCID 713FormamideHCID 6342AcetonitrileHCID 516892Sodium BicarbonateHCID 5049666Sodium triacetoxyborohydrideHCID 67399550HCID 67399550, Verbindung

Produkt 1

HCID 67400002(5R)-5-{(E)-2-(4-tert-butylphenyl)-2-[5-(dimethylamino)-6-methoxypyridin-2-yl]ethenyl}pyrrolidin-2-one

Versuchsvorschrift

A 37% formamide solution (40 μL) was added to a solution of (5R)-5-[(E)-2-(5-amino-6-methoxypyridin-2-yl)-2-(4-tert-butylphenyl)ethenyl]pyrrolidin-2-one obtained in Example 4-173(2) (40 mg) in acetonitrile (2 mL) under ice-cooling, followed by stirring for 10 minutes. Sodium triacetoxyborohydride (120 mg) was added thereto and the mixture was stirred at room temperature for 15 hours. Saturated aqueous sodium bicarbonate was added to the reaction solution, followed by extraction with ethyl acetate. The organic layer was washed with brine and dried over anhydrous sodium sulfate, after which the solvent was evaporated under reduced pressure to give (5R)-5-{(E)-2-(4-tert-butylphenyl)-2-[5-(dimethylamino)-6-methoxypyridin-2-yl]ethenyl}pyrrolidin-2-one as a yellow oil (41 mg).

Aufarbeitung

  1. temperaturecooling
  2. stirringthe mixture was stirred at room temperature for 15 hours
  3. extractionfollowed by extraction with ethyl acetate
  4. washThe organic layer was washed with brine
  5. dry with materialdried over anhydrous sodium sulfate
  6. customafter which the solvent was evaporated under reduced pressure

Quellen und Nachweise

ORD-Eintrag
ord-237b59d9315147ae833ae00b60489882
Quelldatensatz
uspto-grants-2014_09
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US08822503B2

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