HCID 57592135, compound → HCID 57592119, compound

HRID 1784336Notes

Reaction equation

HRID 1784336 reaction equation
[F:1][CH2:2][CH:3]([OH:13])[CH:4]([N+:10]([O-])=O)[CH2:5][CH2:6][C:7]([NH2:9])=[O:8]>CO.[Ni]>[NH2:10][CH:4]([CH:3]([OH:13])[CH2:2][F:1])[CH2:5][CH2:6][C:7]([NH2:9])=[O:8]

Participants

4

Reactant 1

HCID 57592135HCID 57592135, compound

Product 1

HCID 57592119HCID 57592119, compound

Reagents, catalysts & solvents 2

HCID 935NickelCatalystHCID 887MethanolSolvent

Procedure

To a solution of 6-fluoro-5-hydroxy-4-nitro-hexanoic acid amide (0.5 g, 2.58 mmol) in MeOH (20 mL) was added Raney Ni (about 200 mg), and the mixture was shaken under H2 (40-45 psi) at room temperature for 6 h. It was filtered and the catalyst was washed with MeOH (3×10 mL). The MeOH solution was evaporated and the residue oil (435 mg) was used without further purification. 1H NMR (acetone-d6): 6.85 (bs, NH, 1H), 6.15 (bs, NH, 1H), 4.70-4.25 (m, 3H), 3.65-3.50 (m, 1H), 2.86 (bs, 2H), 2.40-2.20 (m, 4H).

Workup

  1. filtrationIt was filtered
  2. washthe catalyst was washed with MeOH (3×10 mL)
  3. customThe MeOH solution was evaporated
  4. customthe residue oil (435 mg) was used without further purification

Sources & evidence

ORD record
ord-e3c4ef72c9b34055b5a306d0ac722329
Source dataset
uspto-grants-2009_03
Patent number
US07504382B2

Reaction notes

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