HCID 86640212, compound → HCID 67002108, compound

HRID 1804417Notes

Reaction equation

HRID 1804417 reaction equation
[CH2:1]([CH2:3][C:4]([O:7][C:8]1[CH:13]=[CH:12][C:11]([CH2:14][CH2:15][N:16]=[N+]=[N-])=[CH:10][CH:9]=1)([CH3:6])[CH3:5])[CH3:2]>CO.[Pd]>[CH2:1]([CH2:3][C:4]([O:7][C:8]1[CH:9]=[CH:10][C:11]([CH2:14][CH2:15][NH2:16])=[CH:12][CH:13]=1)([CH3:5])[CH3:6])[CH3:2]

Participants

4

Reactant 1

HCID 86640212HCID 86640212, compound

Product 1

HCID 67002108HCID 67002108, compoundYield 76.8%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

Pd/C at 10% (16 mg) is added to a solution of ethyl 2-[4-(2-azidoethyl)phenoxy]-2-methylpropane (784 mg, 2.89 mM) in methanol (42 ml) and the suspension is maintained in agitation for the whole night at a pressure of 5 atmospheres of H2 at room temperature until the substrate disappears [TLC (silica gel; mobile phase: ethyl acetate/petroleum ether=2:8)]. The mixture is filtered to remove the catalyst and the solvent is removed at reduced pressure. 539 mg of ethyl 2-[4-(2-aminoethyl)phenoxy]-2-methylpropane is obtained as a colorless oil (74% of yield).

Workup

  1. filtrationThe mixture is filtered
  2. customto remove the catalyst
  3. customthe solvent is removed at reduced pressure

Sources & evidence

ORD record
ord-2c2bcef5f26644cdaf68a9ef8a203c30
Source dataset
uspto-grants-2013_01
Patent number
US08354412B2

Reaction notes

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