Ethylenediamine → (R)-3'-(4-Bromothiophen-2-yl)spiro[1-azabicyclo[2.2.2]octan-3,5'-oxazolidin]-2'-one

HRID 2109425Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 2109425
[O:1]1[C@@:5]2([CH:10]3[CH2:11][CH2:12][N:7]([CH2:8][CH2:9]3)[CH2:6]2)[CH2:4][NH:3][C:2]1=[O:13].Br[C:15]1[S:16][CH:17]=[C:18]([Br:20])[CH:19]=1.C(=O)([O-])[O-].[K+].[K+].C(N)CN>O1CCOCC1.[Cu]I>[Br:20][C:18]1[CH:19]=[C:15]([N:3]2[CH2:4][C@:5]3([CH:10]4[CH2:11][CH2:12][N:7]([CH2:8][CH2:9]4)[CH2:6]3)[O:1][C:2]2=[O:13])[S:16][CH:17]=1

Komponenten

7

Edukt 4

HCID 3301EthylenediamineHCID 11430Potassium CarbonateHCID 2724560Thiophene, 2,4-dibromo-HCID 5310971AR-R-17779

Produkt 1

HCID 57634260(R)-3'-(4-Bromothiophen-2-yl)spiro[1-azabicyclo[2.2.2]octan-3,5'-oxazolidin]-2'-oneAusbeute 63,2 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 24350Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)KatalysatorHCID 312751,4-DioxaneLösungsmittel

Versuchsvorschrift

(S)-Spiro[1-azabicyclo[2.2.2]octan-3,5′-oxazolidin]-2′-one (471 mg, 2.58 mmol), 2,4-dibromothiophene (1.875 g, 7.75 mmole), copper (I) iodide (492 mg, 2.58 mmol), potassium carbonate (715 mg, 5.17 mmol) and ethylenediamine (170 μL, 2.58 mmol) in 1,4-dioxane (5 mL) were stirred at 110° C. overnight. The solution was allowed to cool, and then filtered, washed with aqueous ammonium hydroxide and evaporated. The residue was purified by flash chromatography using a gradient of ammoniated methanol in chloroform to give the title compound as a yellow solid (560 mg), m/z 343, 345 (MH+).

Aufarbeitung

  1. temperatureto cool
  2. filtrationfiltered
  3. washwashed with aqueous ammonium hydroxide
  4. customevaporated
  5. customThe residue was purified by flash chromatography

Quellen und Nachweise

ORD-Eintrag
ord-baaf5c4ddb024d939a8bda0714de2818
Quelldatensatz
uspto-grants-2009_04
Patentnummer
US07514567B2

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