Ammonium formate → Tert-butyl 4-amino-5-(3-methoxyphenyl)valerate

HRID 274074Notes

Reaction equation

HRID 274074 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[C:5]([CH2:9][CH:10]([N+:20]([O-])=O)[CH2:11][CH2:12][C:13]([O:15][C:16]([CH3:19])([CH3:18])[CH3:17])=[O:14])[CH:6]=[CH:7][CH:8]=1.C([O-])=O.[NH4+]>[Pd].CO>[NH2:20][CH:10]([CH2:9][C:5]1[CH:6]=[CH:7][CH:8]=[C:3]([O:2][CH3:1])[CH:4]=1)[CH2:11][CH2:12][C:13]([O:15][C:16]([CH3:19])([CH3:18])[CH3:17])=[O:14]

Participants

5

Reactant 2

HCID 2723923Ammonium formateHCID 20094814Tert-butyl 5-(3-methoxyphenyl)-4-nitrovalerate

Product 1

HCID 20094831Tert-butyl 4-amino-5-(3-methoxyphenyl)valerateYield 87.5%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

A mixture of tert-butyl 5-(3-methoxyphenyl)-4-nitrovalerate (0.31 g), 10% palladium on carbon (0.31 g), and ammonium formate (0.63 g) in methanol (3.1 ml) was stirred at ambient temperature for 0.5 hour. After the insoluble material was removed by filtration, the filtrate was evaporated in vacuo. To the residue, ethyl acetate and water were added and the organic layer was separated. The aqueous layer was extracted with ethyl acetate and the combined organic layer was washed with brine, dried over anhydrous sodium sulfate, and evaporated in vacuo to give tert-butyl 4-amino-5-(3-methoxyphenyl)valerate (245 mg).

Workup

  1. customAfter the insoluble material was removed by filtration
  2. customthe filtrate was evaporated in vacuo
  3. additionTo the residue, ethyl acetate and water were added
  4. customthe organic layer was separated
  5. extractionThe aqueous layer was extracted with ethyl acetate
  6. washthe combined organic layer was washed with brine
  7. dry with materialdried over anhydrous sodium sulfate
  8. customevaporated in vacuo

Sources & evidence

ORD record
ord-f4710edafa374c63828def648c0b4a6e
Source dataset
uspto-grants-1995_02
Patent number
US05387710

Reaction notes

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