HCID 70014587, compound → HCID 15549734, compound

HRID 430479Notes

Reaction equation

HRID 430479 reaction equation
[CH2:1]([CH:5]([C:11](=[O:21])[C:12]1[CH:17]=[CH:16][CH:15]=[C:14]([N+:18]([O-])=O)[CH:13]=1)[C:6]([O:8][CH2:9][CH3:10])=[O:7])[CH:2]=[CH:3][CH3:4]>O1CCOCC1.[Pd].[O-]S([O-])(=O)=O.[Ba+2]>[NH2:18][C:14]1[CH:13]=[C:12]([C:11](=[O:21])[CH:5]([CH2:1][CH2:2][CH2:3][CH3:4])[C:6]([O:8][CH2:9][CH3:10])=[O:7])[CH:17]=[CH:16][CH:15]=1

Participants

4

Reactant 1

HCID 70014587HCID 70014587, compound

Product 1

HCID 15549734HCID 15549734, compoundYield 65.2%

Reagents, catalysts & solvents 2

HCID 16218511Pd barium sulfateCatalystHCID 312751,4-DioxaneSolvent

Procedure

A solution of ethyl α-(2-butenyl)-3-nitro-β-oxobenzenepropanoate (411 mg, 1.41 mmol) in 1,4-dioxane (12 mL) was stirred at 25° for 8.5 h under a hydrogen atmosphere (1 atm) in presence of Pd/BaSO4 (225 mg+150 mg added after 5.5 h). The suspension was filtered (50μ filter) and the filtrate was concentrated under reduced pressure. The residue was purified by flash chromatography (40-63μ silica gel, hexane:EtOAc, 3:1) to give ethyl 3-amino-α-butyl-β-oxobenzenepropionate (242 mg, 65% yield):

Workup

  1. filtrationThe suspension was filtered
  2. filtration(50μ filter)
  3. concentrationthe filtrate was concentrated under reduced pressure
  4. customThe residue was purified by flash chromatography (40-63μ silica gel, hexane:EtOAc, 3:1)

Sources & evidence

ORD record
ord-59af974269d34141a663b138d8524de2
Source dataset
uspto-grants-2001_11
Patent number
US06323202B1

Reaction notes

Loading…