HCID 53902714, compound → HCID 67008394, compound

HRID 1256943Notes

Reaction equation

HRID 1256943 reaction equation
[C:1]([CH:3]([C:10]1[CH:15]=[CH:14][CH:13]=[C:12]([O:16][CH3:17])[CH:11]=1)[CH2:4][C:5]([O:7][CH2:8][CH3:9])=[O:6])#[N:2]>C(O)C.Cl.[H][H].[OH-].[OH-].[Pd+2]>[NH2:2][CH2:1][CH:3]([C:10]1[CH:15]=[CH:14][CH:13]=[C:12]([O:16][CH3:17])[CH:11]=1)[CH2:4][C:5]([O:7][CH2:8][CH3:9])=[O:6]

Participants

6

Reactant 1

HCID 53902714HCID 53902714, compound

Product 1

HCID 67008394HCID 67008394, compoundYield 31.4%

Reagents, catalysts & solvents 4

HCID 9942167Palladium hydroxideCatalystHCID 313Hydrochloric AcidSolventHCID 702EthanolSolventHCID 178418361HCID 178418361, compoundSolvent

Procedure

To a solution of ethyl 3-cyano-3-(3-methoxyphenyl)propanoate (11.9 g) in ethanol (41 ml), 12 N hydrochloric acid (3.8 ml) and 20% palladium hydroxide on carbon (2.10 g) was added, and the mixed solution was stirred in hydrogen atmosphere at room temperature for 15 hours. The solvent was removed by evaporation under reduced pressure, and resulting crude product was purified by column chromatography (neutral OH type silica gel, methanol/chloroform=2 to 9%) to give ethyl 4-amino-3-(3-methoxyphenyl)butanoate (3.80 g).

Workup

  1. customThe solvent was removed by evaporation under reduced pressure
  2. customresulting crude product
  3. customwas purified by column chromatography (neutral OH type silica gel, methanol/chloroform=2 to 9%)

Sources & evidence

ORD record
ord-e30634b378f34fcb8e20ce954207ba63
Source dataset
uspto-grants-2013_06
Patent number
US08461329B2

Reaction notes

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