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

HRID 1741031ノート

反応式

HRID 1741031 の反応式
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

参加物

5

反応物 2

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

生成物 1

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

試薬・触媒・溶媒 2

HCID 6547Azobisisobutyronitrile触媒HCID 241Benzene溶媒2 回

実験手順

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.

後処理

  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)

出典と根拠

ORDレコード
ord-032ce43239024060a8107faab822c06d
出典データセット
uspto-grants-1999_10
特許番号
US05972951

反応ノート

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