Ammonium formate → HCID 14199169, compound

HRID 2372554Notes

Reaction equation

HRID 2372554 reaction equation
[F:1][C:2]([F:18])([F:17])[C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][C:4]=1[CH:9]([OH:16])[CH:10]([N+:13]([O-])=O)[CH2:11][CH3:12].C([O-])=O.[NH4+]>C1COCC1.CO.[Pd].CCOCC>[F:1][C:2]([F:17])([F:18])[C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][C:4]=1[CH:9]([OH:16])[CH:10]([NH2:13])[CH2:11][CH3:12]

Participants

7

Reactant 2

HCID 2723923Ammonium formateHCID 14199167HCID 14199167, compound

Product 1

HCID 14199169HCID 14199169, compound

Reagents, catalysts & solvents 4

HCID 23938PalladiumCatalystHCID 887MethanolSolventHCID 3283Diethyl EtherSolventHCID 8028TetrahydrofuranSolvent

Procedure

To a solution of etythro 1-(2-trifluoromethylphenyl)-2-nitro-butan-1-ol (0.18 g, 0.00068 mole) in THF (5 mL) and methanol (5 mL) was added 10% palladium on carbon (50 mg) followed by ammonium formate (0.21 g, 5 equivalents). The resulting mixture was stirred at room temperature for 1.5 hour then diluted with Et2O, filtered and evaporated in vacuo. Flash column chromatography (SiO2, 2% MeOH in CHCl3) gave erythro 1-(2-trifluoromethylphenyl)-2-amino-butan-1-ol. (0.074 g, 47%), and some starting material (0.035 g).

Workup

  1. filtrationfiltered
  2. customevaporated in vacuo

Sources & evidence

ORD record
ord-c6d48716ca3542e4898ae17c4e982f02
Source dataset
uspto-grants-1992_03
Patent number
US05099067

Reaction notes

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