2,4-Dimethoxybenzylamine → Methyl 2-(3-(2,4-dimethoxybenzylamino)cyclobutyl)acetate

HRID 1404375Notes

Reaction equation

HRID 1404375 reaction equation
O=[C:2]1[CH2:5][CH:4]([CH2:6][C:7]([O:9][CH3:10])=[O:8])[CH2:3]1.[CH3:11][O:12][C:13]1[CH:18]=[C:17]([O:19][CH3:20])[CH:16]=[CH:15][C:14]=1[CH2:21][NH2:22]>[Pd].CO>[CH3:11][O:12][C:13]1[CH:18]=[C:17]([O:19][CH3:20])[CH:16]=[CH:15][C:14]=1[CH2:21][NH:22][CH:2]1[CH2:5][CH:4]([CH2:6][C:7]([O:9][CH3:10])=[O:8])[CH2:3]1

Participants

5

Reactant 2

HCID 5972502,4-DimethoxybenzylamineHCID 57686718Methyl 2-(3-oxocyclobutyl)acetate

Product 1

HCID 86722980Methyl 2-(3-(2,4-dimethoxybenzylamino)cyclobutyl)acetateYield 96.7%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

To methyl 2-(3-oxocyclobutyl)acetate (426 mg) and (2,4-dimethoxyphenyl)methanamine (501 mg) in a flask was added MeOH (20 mL) and Pd/C (10%, 100 mg). The reaction mixture was stirred under hydrogen atmosphere for overnight. Catalyst was removed by filtration through the Celite pad. Removal of the solvent afforded the crude product (850 mg) which was used directly to the next step without further purification.

Workup

  1. customCatalyst was removed by filtration through the Celite pad
  2. customRemoval of the solvent

Sources & evidence

ORD record
ord-5bb4f1d4744f48f28d4f81e3eb256e56
Source dataset
uspto-grants-2014_12
Patent number
US08912169B2

Reaction notes

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