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

HRID 1741031Notes

Reaction equation

HRID 1741031 reaction equation
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

Participants

5

Reactant 2

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

Product 1

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

Reagents, catalysts & solvents 2

HCID 6547AzobisisobutyronitrileCatalystHCID 241BenzeneSolvent2×

Procedure

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.

Workup

  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)

Sources & evidence

ORD record
ord-032ce43239024060a8107faab822c06d
Source dataset
uspto-grants-1999_10
Patent number
US05972951

Reaction notes

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