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

HRID 453542Notes

Reaction equation

HRID 453542 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 62.8%

Reagents, catalysts & solvents 2

HCID 935NickelCatalystHCID 21705897Ammonia methanolSolvent

Procedure

To a stirred solution of the methyl 4-(4-(2-tert-butoxy-2-oxoethyl)-2-cyanophenoxy)benzoate (1.086 mg, 2.96 mmol) in 7N ammonia/methanol (30 ml) under nitrogen was added Raney Nickel (25.3 mg, 0.296 mmol). The reaction was purged with a hydrogen balloon and stirred under hydrogen overnight. The reaction was filtered through GF paper and the solid catalyst was rinsed with methanol and ethyl acetate. The filtrate was concentrated, and the crude product was purified by silica gel chromatography to give methyl 4-(2-(aminomethyl)-4-(2-tert-butoxy-2-oxoethyl)phenoxy)benzoate (0.69 g).

Workup

  1. customThe reaction was purged with a hydrogen balloon
  2. filtrationThe reaction was filtered through GF paper
  3. washthe solid catalyst was rinsed with methanol and ethyl acetate
  4. concentrationThe filtrate was concentrated
  5. customthe crude product was purified by silica gel chromatography

Sources & evidence

ORD record
ord-c8ec6934a1644c05981507c4df3dc4cb
Source dataset
uspto-grants-2013_07
Patent number
US08492437B2

Reaction notes

Loading…