HCID 59464125, compound → HCID 59464224, compound

HRID 1713890Notes

Reaction equation

HRID 1713890 reaction equation
C(O[C:9]([NH:11][C:12]1[CH:17]=[CH:16][C:15]([CH:18]2[CH2:23][CH2:22][C:21](=[C:24]([CH3:30])[C:25]([O:27][CH2:28][CH3:29])=[O:26])[CH2:20][CH2:19]2)=[C:14]([Cl:31])[CH:13]=1)=[O:10])C1C=CC=CC=1>C(OCC)(=O)C.[Pt]=O>[Cl:31][C:14]1[CH:13]=[C:12]([NH:11][C:9](=[O:10])[C:25]([O:27][CH3:28])=[O:26])[CH:17]=[CH:16][C:15]=1[CH:18]1[CH2:23][CH2:22][CH:21]([CH:24]([CH3:30])[C:25]([O:27][CH2:28][CH3:29])=[O:26])[CH2:20][CH2:19]1

Participants

4

Reactant 1

HCID 59464125HCID 59464125, compound

Product 1

HCID 59464224HCID 59464224, compound

Reagents, catalysts & solvents 2

HCID 82844Platinum oxide (PtO)Catalyst2×HCID 8857Ethyl AcetateSolvent

Procedure

Platinum oxide (300 mg) was added in one portion to a stirred solution of ethyl 2-[4-(4-{[(benzyloxy)carbonyl]amino}-2-chlorophenyl)cyclohexylidene]propanoate (1.5 g, 3.39 mmol) in ethyl acetate (30 mL) and the mixture was stirred at room temperature under a hydrogen atmosphere for 7 h. A further portion of platinum oxide (1.0 g) was added in one portion and the mixture was stirred for 1 h at room temperature under a hydrogen atmosphere. The reaction mixture was filtered and concentrated in vacuo to leave a residue, which was purified by column chromatography, using a gradient of 11-50% ethyl acetate:isohexane as eluent, to give the aniline product as a mixture of cis- and trans-cyclohexane isomers, that was used with no further purification.

Workup

  1. stirringthe mixture was stirred for 1 h at room temperature under a hydrogen atmosphere
  2. filtrationThe reaction mixture was filtered
  3. concentrationconcentrated in vacuo
  4. customto leave a residue, which
  5. customwas purified by column chromatography

Sources & evidence

ORD record
ord-c2950ca1fda94cae8e7b3f59733d4514
Source dataset
uspto-grants-2010_09
Patent number
US07795283B2

Reaction notes

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