HCID 15596441, compound → HCID 23049317, compound

HRID 2106860Notes

Reaction equation

HRID 2106860 reaction equation
[CH2:1]([NH:5][C:6](=[O:19])/[CH:7]=[CH:8]/[CH2:9][CH2:10][C:11]#[C:12][C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1)[CH:2]([CH3:4])[CH3:3]>CO.[Pd]>[CH2:1]([NH:5][C:6](=[O:19])/[CH:7]=[CH:8]/[CH2:9][CH2:10][CH2:11][CH2:12][C:13]1[CH:14]=[CH:15][CH:16]=[CH:17][CH:18]=1)[CH:2]([CH3:4])[CH3:3]

Participants

4

Reactant 1

HCID 15596441HCID 15596441, compound

Product 1

HCID 23049317HCID 23049317, compoundYield 66.9%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent2×

Procedure

The product of Example 1 (100 mg) was dissolved in dry methanol (3 ml), 5% Pd/C (25 mg) was added, and the mixture was hydrogenated at atmospheric pressure and room temperature. The reaction mixture was diluted with methanol and filtered. The solvent was removed in vacuo, and ether was added then removed in a stream of nitrogen. The last traces of solvent were removed in vacuo to yield N-isobutyl-7-phenylhept-2E-enamide (68 mg). Refractive index 1.39.

Workup

  1. customwas hydrogenated at atmospheric pressure and room temperature
  2. filtrationfiltered
  3. customThe solvent was removed in vacuo, and ether
  4. additionwas added
  5. customthen removed in a stream of nitrogen
  6. customThe last traces of solvent were removed in vacuo

Sources & evidence

ORD record
ord-92f5f5421d0742ac8476ef7f54d7782d
Source dataset
uspto-grants-1990_06
Patent number
US04931469

Reaction notes

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