Ammonium formate → HCID 59786573, compound

HRID 1661486Notes

Reaction equation

HRID 1661486 reaction equation
C([O-])=O.[NH4+].[CH3:5][O:6][C:7]1[CH:12]=[C:11]([CH:13]([OH:20])[CH:14]([N+:17]([O-])=O)[CH2:15][CH3:16])[CH:10]=[CH:9][N:8]=1>[Pd].C1COCC1.CO>[NH2:17][CH:14]([CH2:15][CH3:16])[CH:13]([C:11]1[CH:10]=[CH:9][N:8]=[C:7]([O:6][CH3:5])[CH:12]=1)[OH:20]

Participants

6

Reactant 2

HCID 2723923Ammonium formateHCID 59786578HCID 59786578, compound

Product 1

HCID 59786573HCID 59786573, compound

Reagents, catalysts & solvents 3

HCID 23938PalladiumCatalystHCID 887MethanolSolventHCID 8028TetrahydrofuranSolvent

Procedure

Ammonium formate (2.5 g, 40 mmol) and palladium on charcoal (10%, 390 mg) is added to a solution of 1-(2-methoxypyridin-4-yl)-2-nitrobutan-1-ol (1.7 g, 7.5 mmol) in 38 ml THF and 38 ml methanol. The reaction mixture is stirred overnight at room temperature, filtered through a path of cellites and concentrated. Yield 620 mg of a racemic mixture of two diastereomers, 42%.

Workup

  1. filtrationfiltered through a path of cellites
  2. concentrationconcentrated

Sources & evidence

ORD record
ord-7a1db06e3c6246fd8d172534b395f5dd
Source dataset
uspto-grants-2011_10
Patent number
US08030340B2

Reaction notes

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