6-Fluoro-5-hydroxy-4-nitro-hexanoic acid dimethylamide → 4-Amino-6-Fluoro-5-Hydroxy-Hexanoic Acid Dimethylamide

HRID 1784343Notes

Reaction equation

HRID 1784343 reaction equation
[CH3:1][N:2]([CH3:15])[C:3](=[O:14])[CH2:4][CH2:5][CH:6]([N+:11]([O-])=O)[CH:7]([OH:10])[CH2:8][F:9]>CO.[Ni]>[CH3:15][N:2]([CH3:1])[C:3](=[O:14])[CH2:4][CH2:5][CH:6]([NH2:11])[CH:7]([OH:10])[CH2:8][F:9]

Participants

4

Reactant 1

HCID 453582006-Fluoro-5-hydroxy-4-nitro-hexanoic acid dimethylamide

Product 1

HCID 575921364-Amino-6-Fluoro-5-Hydroxy-Hexanoic Acid DimethylamideYield 87%

Reagents, catalysts & solvents 2

HCID 935NickelCatalystHCID 887MethanolSolvent

Procedure

To a solution of 6-fluoro-5-hydroxy-4-nitro-hexanoic acid dimethylamide (1.22 g, 5.5 mmol) in MeOH (20 mL) was added Ranny Ni (about 500 mg), and the mixture was hydrogenated under 40-45 psi H2 at room temperature for 6 h. The catalyst was removed. The MeOH solution was evaporated and the residue oil (0.92 g, yield 87%) was used without further purification. MS m/e 193 (M+1).

Workup

  1. customThe catalyst was removed
  2. customThe MeOH solution was evaporated

Sources & evidence

ORD record
ord-96b8dad7630b44038b0ed037edf7fea9
Source dataset
uspto-grants-2009_03
Patent number
US07504382B2

Reaction notes

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