HCID 59179737, compound → HCID 178472466, compound

HRID 1675334Notes

Reaction equation

HRID 1675334 reaction equation
[CH2:1]([O:3][C:4]([CH:6]1[CH2:11][CH2:10][CH:9]([O:12][C:13]2[CH:18]=[CH:17][C:16]([N+:19]([O-])=O)=[C:15]([F:22])[CH:14]=2)[CH2:8][CH2:7]1)=[O:5])[CH3:2]>C(O)C.[Pd]>[CH2:1]([O:3][C:4]([C@H:6]1[CH2:11][CH2:10][C@@H:9]([O:12][C:13]2[CH:18]=[CH:17][C:16]([NH2:19])=[C:15]([F:22])[CH:14]=2)[CH2:8][CH2:7]1)=[O:5])[CH3:2]

Participants

4

Reactant 1

HCID 59179737HCID 59179737, compound

Product 1

HCID 178472466HCID 178472466, compoundYield 85.1%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

Palladium (10 wt. %) on carbon (500 mg) was added in one portion to a solution of 4-(3-fluoro-4-nitro-phenoxy)-cyclohexanecarboxylic acid ethyl ester (2.6 g, 8.35 mmol) in ethanol (75 mL) and the mixture was stirred under a hydrogen atmosphere for 6 h. The reaction mixture was filtered and concentrated in vacuo to leave a residue. The residue was purified by column chromatography, using a gradient of 20-50% EtOAc and isohexane as eluent, to give the title compound as a pale yellow solid (2.0 g, 85%)

Workup

  1. filtrationThe reaction mixture was filtered
  2. concentrationconcentrated in vacuo
  3. customto leave a residue
  4. customThe residue was purified by column chromatography

Sources & evidence

ORD record
ord-449dca19c5694ea2b30f24e1abc90220
Source dataset
uspto-grants-2011_08
Patent number
US08003676B2

Reaction notes

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