3-Bromo-5-phenylpyridine → Ethyl 6-hydroxy-6-(5-phenyl-3-pyridinyl)-3-azabicyclo[3.2.1]octane-3-carboxylate

HRID 597999

Reaktionsgleichung

Reaktionsgleichung von HRID 597999
Br[C:2]1[CH:3]=[N:4][CH:5]=[C:6]([C:8]2[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=2)[CH:7]=1.C([Mg]Cl)(C)C.[O:19]=[C:20]1[CH2:26][CH:25]2[CH2:27][CH:21]1[CH2:22][N:23]([C:28]([O:30][CH2:31][CH3:32])=[O:29])[CH2:24]2>C1COCC1>[OH:19][C:20]1([C:2]2[CH:3]=[N:4][CH:5]=[C:6]([C:8]3[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=3)[CH:7]=2)[CH2:26][CH:25]2[CH2:27][CH:21]1[CH2:22][N:23]([C:28]([O:30][CH2:31][CH3:32])=[O:29])[CH2:24]2

Komponenten

5

Edukt 3

HCID 27629043-Bromo-5-phenylpyridineHCID 53302214Ethyl 6-oxo-3-azabicyclo(3.2.1)octane-3-carboxylateHCID 178418918HCID 178418918, Verbindung

Produkt 1

HCID 57486356Ethyl 6-hydroxy-6-(5-phenyl-3-pyridinyl)-3-azabicyclo[3.2.1]octane-3-carboxylateAusbeute 14,2 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8028TetrahydrofuranLösungsmittel3×

Versuchsvorschrift

To a solution of 3-bromo-5-phenylpyridine (0.23 g, 1.0 mmol) in THF (5 mL) at ambient temperature was added 2.0 M isopropylmagnesium chloride in THF (0.5 mL). The reaction was stirred for an hour under nitrogen. Then a solution of ethyl 6-oxo-3-azabicyclo[3.2.1]octane-3-carboxylate (0.21 g, 1.0 mmol) in THF (2 mL) was added. The mixture was stirred at ambient temperature overnight, concentrated and quenched with water (1 mL). The mixture was extracted with chloroform (2×10 mL), and the combined extracts were dried over magnesium sulfate, filtered, and concentrated by rotary evaporation. The compound was purified by silica gel column chromatography (1:1 ethyl acetate/hexane) to yield 50 mg of product (13%).

Aufarbeitung

  1. stirringThe mixture was stirred at ambient temperature overnight
  2. concentrationconcentrated
  3. customquenched with water (1 mL)
  4. extractionThe mixture was extracted with chloroform (2×10 mL)
  5. dry with materialthe combined extracts were dried over magnesium sulfate
  6. filtrationfiltered
  7. concentrationconcentrated by rotary evaporation
  8. customThe compound was purified by silica gel column chromatography (1:1 ethyl acetate/hexane)

Quellen und Nachweise

ORD-Eintrag
ord-a4b8d850f384478e96d4fdd1ea523ea9
Quelldatensatz
uspto-grants-2011_03
Patentnummer
US07897611B2

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