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

HRID 1486188Notes

Reaction equation

HRID 1486188 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-316ee79ea637487faa4620d5151d7ae4
Source dataset
uspto-grants-2016_08
Patent number
US09422314B2

Reaction notes

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