Tributylstannane → 1'-Methyl-2H-spiro[benzofuran-3,4'-piperidine]

HRID 1741031Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1741031
I[C:2]1[CH:16]=[CH:15][CH:14]=[CH:13][C:3]=1[O:4][CH2:5][C:6]1[CH2:7][CH2:8][N:9]([CH3:12])[CH2:10][CH:11]=1.C([SnH](CCCC)CCCC)CCC>C1C=CC=CC=1.CC(N=NC(C#N)(C)C)(C#N)C>[CH3:12][N:9]1[CH2:8][CH2:7][C:6]2([C:2]3[CH:16]=[CH:15][CH:14]=[CH:13][C:3]=3[O:4][CH2:5]2)[CH2:11][CH2:10]1

Komponenten

5

Edukt 2

HCID 5948TributylstannaneHCID 107350934-(2-Iodophenoxymethyl)-1-methyl-1,2,3,6-tetrahydropyridine

Produkt 1

HCID 104883751'-Methyl-2H-spiro[benzofuran-3,4'-piperidine]Ausbeute 73 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 6547AzobisisobutyronitrileKatalysatorHCID 241BenzeneLösungsmittel2×

Versuchsvorschrift

4-(2-Iodophenoxymethyl)-1-methyl-1,2,3,6-tetrahydropyridine (D2, 8.72 g, 0.026 mol) and AIBN (0.20 g, 0.0012 mol) were stirred at reflux under Ar in benzene (500 ml) as tributyltin hydride (14.3 ml, 0.053 mol) was added dropwise in benzene (100 ml) over 1 h. The mixture was stirred at reflux for a further 4.5 h, cooled and evaporated. The residue was dissolved in ethyl acetate, and extracted with dil. HCl. The extract was basified (sat. K2CO3 solution) and extracted with ethyl acetate. This organic extract was dried (Na2SO4) and evaporated to give a brown solid, which was chromatographed on silica gel, eluting with 0-8% methanol/chloroform (gradient) to give the title compound (3.86 g, 69%) as a light yellow solid.

Aufarbeitung

  1. temperatureat reflux for a further 4.5 h
  2. temperaturecooled
  3. customevaporated
  4. dissolutionThe residue was dissolved in ethyl acetate
  5. extractionextracted with dil. HCl
  6. extractionextracted with ethyl acetate
  7. extractionThis organic extract
  8. dry with materialwas dried (Na2SO4)
  9. customevaporated
  10. customto give a brown solid, which
  11. customwas chromatographed on silica gel
  12. washeluting with 0-8% methanol/chloroform (gradient)

Quellen und Nachweise

ORD-Eintrag
ord-032ce43239024060a8107faab822c06d
Quelldatensatz
uspto-grants-1999_10
Patentnummer
US05972951

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