Methyl 4-(4-(2-tert-butoxy-2-oxoethyl)-2-cyanophenoxy)benzoate → Methyl 4-(2-(aminomethyl)-4-(2-tert-butoxy-2-oxoethyl)phenoxy)benzoate

HRID 1927722Notes

Reaction equation

HRID 1927722 reaction equation
[C:1]([O:5][C:6](=[O:27])[CH2:7][C:8]1[CH:24]=[CH:23][C:11]([O:12][C:13]2[CH:22]=[CH:21][C:16]([C:17]([O:19][CH3:20])=[O:18])=[CH:15][CH:14]=2)=[C:10]([C:25]#[N:26])[CH:9]=1)([CH3:4])([CH3:3])[CH3:2]>N.CO.[Ni]>[NH2:26][CH2:25][C:10]1[CH:9]=[C:8]([CH2:7][C:6]([O:5][C:1]([CH3:4])([CH3:3])[CH3:2])=[O:27])[CH:24]=[CH:23][C:11]=1[O:12][C:13]1[CH:14]=[CH:15][C:16]([C:17]([O:19][CH3:20])=[O:18])=[CH:21][CH:22]=1

Participants

4

Reactant 1

HCID 68466372Methyl 4-(4-(2-tert-butoxy-2-oxoethyl)-2-cyanophenoxy)benzoate

Product 1

HCID 68464831Methyl 4-(2-(aminomethyl)-4-(2-tert-butoxy-2-oxoethyl)phenoxy)benzoateYield 74%

Reagents, catalysts & solvents 2

HCID 935NickelCatalystHCID 21705897Ammonia methanolSolvent

Procedure

The product of step A (2.5 g, 6.80 mmol) was diluted with 7N ammonia/methanol (30 mL) followed by the addition of Raney Nickel (0.0583 g, 0.680 mmol). The reaction mixture was purged three times with hydrogen and stirred for 12 hours. The reaction mixture was then filtered through a GF/F filter and concentrated. The residue was purified using a biotage 40M column eluting with methylene chloride:MeOH:NH4OH (90:9:1) to yield methyl 4-(2-(aminomethyl)-4-(2-tert-butoxy-2-oxoethyl)phenoxy)benzoate (1.87 g, 74.0% yield) as a clear oil.

Workup

  1. customThe reaction mixture was purged three times with hydrogen
  2. filtrationThe reaction mixture was then filtered through a GF/F
  3. filtrationfilter
  4. concentrationconcentrated
  5. customThe residue was purified
  6. washeluting with methylene chloride:MeOH:NH4OH (90:9:1)

Sources & evidence

ORD record
ord-8532021433b8452c823478a2a2e1d768
Source dataset
uspto-grants-2012_05
Patent number
US08183289B2

Reaction notes

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