Ammonium formate → HCID 14199165, compound

HRID 2372555Notes

Reaction equation

HRID 2372555 reaction equation
[CH3:1][O:2][C:3]([C:5]1[CH:10]=[CH:9][C:8]([CH2:11][C:12]([N+:16]([O-])=O)(O)[CH2:13][CH3:14])=[CH:7][CH:6]=1)=[O:4].C([O-])=[O:20].[NH4+]>C1COCC1.CO.[Pd].CCOCC>[CH3:1][O:2][C:3]([C:5]1[CH:10]=[CH:9][C:8]([CH:11]([OH:20])[CH:12]([NH2:16])[CH2:13][CH3:14])=[CH:7][CH:6]=1)=[O:4]

Participants

7

Reactant 2

HCID 2723923Ammonium formateHCID 19905004HCID 19905004, compound

Product 1

HCID 14199165HCID 14199165, compoundYield 75.8%

Reagents, catalysts & solvents 4

HCID 23938PalladiumCatalystHCID 887MethanolSolventHCID 3283Diethyl EtherSolventHCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 1-(4-methoxycarbonylphenyl)-2-nitro-butan-2-ol (0.34 g, 1.3 mmol) in THF (5 mL) and methanol (5 mL) was added 10% palladium on carbon (50 mg) followed by ammonium formate (0.4 g, 5 equivalents). The resulting mixture was stirred at room temperature for 3 hours ten diluted with Et2O, filtered and evaporated in vacuo. Flash column chromatography (SiO2, 15% MeOH in CHCl3) gave erythro 1-(4-methoxycarbonylphenyl)-2-amino-butan-1-ol (0.22 g, 73%).

Workup

  1. filtrationfiltered
  2. customevaporated in vacuo

Sources & evidence

ORD record
ord-2bc5b58c47bf4faa84a4ad49429b4d3c
Source dataset
uspto-grants-1992_03
Patent number
US05099067

Reaction notes

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