Ethyl 3-cyclopropyl-2-(3(cyclopropylmethoxy)-4-nitrophenyl)propanoate → Ethyl 2-(4-amino-3-(cyclopropylmethoxy)phenyl)-3-cyclopropylpropanoate

HRID 385404Notes

Reaction equation

HRID 385404 reaction equation
[CH:1]1([CH2:4][CH:5]([C:11]2[CH:16]=[CH:15][C:14]([N+:17]([O-])=O)=[C:13]([O:20][CH2:21][CH:22]3[CH2:24][CH2:23]3)[CH:12]=2)[C:6]([O:8][CH2:9][CH3:10])=[O:7])[CH2:3][CH2:2]1>CO.[OH-].[OH-].[Pd+2]>[NH2:17][C:14]1[CH:15]=[CH:16][C:11]([CH:5]([CH2:4][CH:1]2[CH2:2][CH2:3]2)[C:6]([O:8][CH2:9][CH3:10])=[O:7])=[CH:12][C:13]=1[O:20][CH2:21][CH:22]1[CH2:24][CH2:23]1

Participants

4

Reactant 1

HCID 57995591Ethyl 3-cyclopropyl-2-(3(cyclopropylmethoxy)-4-nitrophenyl)propanoate

Product 1

HCID 57995649Ethyl 2-(4-amino-3-(cyclopropylmethoxy)phenyl)-3-cyclopropylpropanoateYield 96.1%

Reagents, catalysts & solvents 2

HCID 9942167Palladium hydroxideCatalystHCID 887MethanolSolvent

Procedure

To a stirred solution of ethyl 3-cyclopropyl-2-(3(cyclopropylmethoxy)-4-nitrophenyl)propanoate (4.0 g), in dry MeOH (100 mL), Pd(OH)2 (2 g) was added and the 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 2-(4-amino-3-(cyclopropylmethoxy)phenyl)-3-cyclopropylpropanoate (3.5 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-db80a4c183be4739a452205fac790c53
Source dataset
uspto-grants-2013_02
Patent number
US08367863B2

Reaction notes

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