1,1'-(Hexane-1,6-diyl)bis{2-[(3,4-dimethoxyphenyl)methyl]-1H-pyrrole} → HCID 19884871, compound

HRID 2372828Notes

Reaction equation

HRID 2372828 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[C:5]([CH:34]=[CH:35][C:36]=1[O:37][CH3:38])[CH2:6][C:7]1[N:8]([CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][N:18]2[CH:22]=[CH:21][CH:20]=[C:19]2[CH2:23][C:24]2[CH:29]=[CH:28][C:27]([O:30][CH3:31])=[C:26]([O:32][CH3:33])[CH:25]=2)[CH:9]=[CH:10][CH:11]=1.[H][H]>C(O)(=O)C.[Rh]>[CH3:33][O:32][C:26]1[CH:25]=[C:24]([CH:29]=[CH:28][C:27]=1[O:30][CH3:31])[CH2:23][CH:19]1[CH2:20][CH2:21][CH2:22][N:18]1[CH2:17][CH2:16][CH2:15][CH2:14][CH2:13][CH2:12][N:8]1[CH2:9][CH2:10][CH2:11][CH:7]1[CH2:6][C:5]1[CH:34]=[CH:35][C:36]([O:37][CH3:38])=[C:3]([O:2][CH3:1])[CH:4]=1

Participants

5

Reactant 2

HCID 198848761,1'-(Hexane-1,6-diyl)bis{2-[(3,4-dimethoxyphenyl)methyl]-1H-pyrrole}HCID 178418361HCID 178418361, compound

Product 1

HCID 19884871HCID 19884871, compoundYield 92%

Reagents, catalysts & solvents 2

HCID 23948RhodiumCatalystHCID 176Acetic AcidSolvent

Procedure

A solution of 1,6-bis[2-(3,4-dimethoxybenzyl)-pyrrol-1-yl]hexane (2.5 g) in glacial acetic acid (30 mL) containing suspended 5% rhodium on alumina catalyst (1.87 g) was reduced at room temperature and an initial hydrogen pressure of 45 p.s.i.g. (3 hour reaction, followed by TLC). The mixture was filtered through Celite. The filtrate was dried at reduced pressure, and the residue dissolved in dichloromethane, washed with ammonium hydroxide solution and dried over sodium sulfate. The solvent was removed in vacuo, and the residue subjected to column chromatographic purification on silica gel (100 g) using dichloromethane, to elute 1,6-bis[2-(3,4-dimethoxybenzyl)pyrrolidin-1-yl]hexane, 2.5 g (92% yield) as an oil.

Workup

  1. customwas reduced at room temperature
  2. custom(3 hour reaction, followed by TLC)
  3. filtrationThe mixture was filtered through Celite
  4. customThe filtrate was dried at reduced pressure
  5. dissolutionthe residue dissolved in dichloromethane
  6. washwashed with ammonium hydroxide solution
  7. dry with materialdried over sodium sulfate
  8. customThe solvent was removed in vacuo
  9. customthe residue subjected to column chromatographic purification on silica gel (100 g)
  10. washto elute 1,6-bis[2-(3,4-dimethoxybenzyl)pyrrolidin-1-yl]hexane, 2.5 g (92% yield) as an oil

Sources & evidence

ORD record
ord-7c9c96568c614396b1a8ad8e959799d3
Source dataset
uspto-grants-1992_03
Patent number
US05100912

Reaction notes

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