Ethyl 4-methyl-2-(4-nitro-3-(2,2,2-trifluoroethoxy)phenyl)pentanoate → Ethyl 2-(4-amino-3-(2,2,2-trifluoroethoxy)phenyl)-4-methylpentanoate

HRID 385437Notes

Reaction equation

HRID 385437 reaction equation
[CH3:1][CH:2]([CH3:25])[CH2:3][CH:4]([C:10]1[CH:15]=[CH:14][C:13]([N+:16]([O-])=O)=[C:12]([O:19][CH2:20][C:21]([F:24])([F:23])[F:22])[CH:11]=1)[C:5]([O:7][CH2:8][CH3:9])=[O:6]>CO.[OH-].[OH-].[Pd+2]>[NH2:16][C:13]1[CH:14]=[CH:15][C:10]([CH:4]([CH2:3][CH:2]([CH3:1])[CH3:25])[C:5]([O:7][CH2:8][CH3:9])=[O:6])=[CH:11][C:12]=1[O:19][CH2:20][C:21]([F:22])([F:23])[F:24]

Participants

4

Reactant 1

HCID 57995623Ethyl 4-methyl-2-(4-nitro-3-(2,2,2-trifluoroethoxy)phenyl)pentanoate

Product 1

HCID 57995581Ethyl 2-(4-amino-3-(2,2,2-trifluoroethoxy)phenyl)-4-methylpentanoateYield 87.2%

Reagents, catalysts & solvents 2

HCID 9942167Palladium hydroxideCatalystHCID 887MethanolSolvent

Procedure

To a stirred solution of ethyl 4-methyl-2-(4-nitro-3-(2,2,2-trifluoroethoxy)phenyl)pentanoate (1.5 g), in dry MeOH (100 mL), Pd(OH)2 (500 mg) was added and the mixture reduced under an atmosphere of H2 for 6 h at room temperature. The mixture was filtered through a pad of Celite™ washing with MeOH. The combined filtrates were concentrated under reduced pressure to give ethyl 2-(4-amino-3-(2,2,2-trifluoroethoxy)phenyl)-4-methylpentanoate (1.2 g) as a thick liquid.

Workup

  1. filtrationThe 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-e4fe53f20f424ab681457a715c75281a
Source dataset
uspto-grants-2013_02
Patent number
US08367863B2

Reaction notes

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