HCID 11026834, compound → HCID 11133671, compound

HRID 1768156Notes

Reaction equation

HRID 1768156 reaction equation
[N+:1]([C:4]1[CH:30]=[CH:29][C:7]([N:8]([CH2:19][CH2:20][O:21][Si:22]([C:25]([CH3:28])([CH3:27])[CH3:26])([CH3:24])[CH3:23])[CH2:9][CH2:10][O:11][Si:12]([C:15]([CH3:18])([CH3:17])[CH3:16])([CH3:14])[CH3:13])=[CH:6][CH:5]=1)([O-])=O>C1COCC1.[Pd]>[NH2:1][C:4]1[CH:30]=[CH:29][C:7]([N:8]([CH2:9][CH2:10][O:11][Si:12]([C:15]([CH3:18])([CH3:17])[CH3:16])([CH3:14])[CH3:13])[CH2:19][CH2:20][O:21][Si:22]([C:25]([CH3:27])([CH3:28])[CH3:26])([CH3:24])[CH3:23])=[CH:6][CH:5]=1

Participants

4

Reactant 1

HCID 11026834HCID 11026834, compound

Product 1

HCID 11133671HCID 11133671, compoundYield 95.3%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 8028TetrahydrofuranSolvent

Procedure

4-Nitro-bis[2′-(tert-butyldimethylsilyloxy)ethyl]-aniline (X-4a) (5.50 g, 12.1 mmol) was dissolved in 90 mL THF, 1.5 g Pd/C 10% was added, and the suspension was stirred under H2 atmosphere for 6 h. The catalyst was then filtered off, the solvent evaporated and the residue purified by column chromatography (cyclohexane:AcOEt 3:1) to yield the title compound (4.90 g, 95%) as an oil.

Workup

  1. filtrationThe catalyst was then filtered off
  2. customthe solvent evaporated
  3. customthe residue purified by column chromatography (cyclohexane:AcOEt 3:1)

Sources & evidence

ORD record
ord-ab70b72f02cd463fb9585b5419e42b0a
Source dataset
uspto-grants-2007_06
Patent number
US07235585B2

Reaction notes

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