Ethyl 1-(3-(cyclopropylmethoxy)-4-nitrophenyl)cyclobutanecarboxylate → Ethyl 1-(4-amino-3-(cyclopropylmethoxy)phenyl)cyclobutanecarboxylate

HRID 385408Notes

Reaction equation

HRID 385408 reaction equation
[CH:1]1([CH2:4][O:5][C:6]2[CH:7]=[C:8]([C:15]3([C:19]([O:21][CH2:22][CH3:23])=[O:20])[CH2:18][CH2:17][CH2:16]3)[CH:9]=[CH:10][C:11]=2[N+:12]([O-])=O)[CH2:3][CH2:2]1>CO.[OH-].[OH-].[Pd+2]>[NH2:12][C:11]1[CH:10]=[CH:9][C:8]([C:15]2([C:19]([O:21][CH2:22][CH3:23])=[O:20])[CH2:18][CH2:17][CH2:16]2)=[CH:7][C:6]=1[O:5][CH2:4][CH:1]1[CH2:3][CH2:2]1

Participants

4

Reactant 1

HCID 57995510Ethyl 1-(3-(cyclopropylmethoxy)-4-nitrophenyl)cyclobutanecarboxylate

Product 1

HCID 57995499Ethyl 1-(4-amino-3-(cyclopropylmethoxy)phenyl)cyclobutanecarboxylateYield 94.6%

Reagents, catalysts & solvents 2

HCID 9942167Palladium hydroxideCatalystHCID 887MethanolSolvent

Procedure

To a stirred solution of ethyl 1-(3-(cyclopropylmethoxy)-4-nitrophenyl)cyclobutanecarboxylate (2.8 g), in dry MeOH (100 mL), Pd(OH)2 (1.2 g) was added and the reaction mixture was reduced under an atmosphere of H2 for 6 h at room temperature. The reaction mixture was filtered through a pad of Celite™ washing with MeOH. The combined filtrates were concentrated under reduced pressure to yield ethyl 1-(4-amino-3-(cyclopropylmethoxy)phenyl)cyclobutanecarboxylate (2.4 g) as a thick liquid.

Workup

  1. filtrationThe reaction mixture was filtered through a pad of Celite™
  2. washwashing with MeOH
  3. concentrationThe combined filtrates were concentrated under reduced pressure

Sources & evidence

ORD record
ord-b316cdaf269b4dcabb74db00fe069c02
Source dataset
uspto-grants-2013_02
Patent number
US08367863B2

Reaction notes

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