HCID 13560812, compound → HCID 13560813, compound

HRID 1285529Notes

Reaction equation

HRID 1285529 reaction equation
[CH3:1][CH:2]([N:4]([CH:24]([CH3:26])[CH3:25])[CH2:5][CH2:6][C:7]([C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1)([CH2:11][C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][N:13]=1)[C:8](N)=[O:9])[CH3:3].[H][H]>C(O)(=O)C.[Pt]=O>[CH3:3][CH:2]([N:4]([CH:24]([CH3:26])[CH3:25])[CH2:5][CH2:6][C:7]1([C:18]2[CH:19]=[CH:20][CH:21]=[CH:22][CH:23]=2)[C:8](=[O:9])[N:13]2[CH:12]([CH2:17][CH2:16][CH2:15][CH2:14]2)[CH2:11]1)[CH3:1]

Participants

5

Reactant 2

HCID 13560812HCID 13560812, compoundHCID 178418361HCID 178418361, compound

Product 1

HCID 13560813HCID 13560813, compoundYield 55.6%

Reagents, catalysts & solvents 2

HCID 82844Platinum oxide (PtO)CatalystHCID 176Acetic AcidSolvent

Procedure

A solution of 11.0 g (31 mmol) of the title product of Example 2 was hydrogenated at room temperature in 200 ml of glacial acetic acid using hydrogen at 60 psi over 1 g of platinum oxide catalyst. After catalyst was removed by filtration, the solvent was removed in vacuo and the residue redissolved in ice/water. The aqueous solution was made basic with dilute aqueous sodium hydroxide and extracted with diethyl ether. The organic layer was washed with brine, dried over magnesium sulfate, filtered, and concentrated in vacuo. Column chromatography on silica gel afforded 5.9 g of the title compound as an analytically pure oil.

Workup

  1. customAfter catalyst was removed by filtration
  2. customthe solvent was removed in vacuo
  3. dissolutionthe residue redissolved in ice/water
  4. extractionextracted with diethyl ether
  5. washThe organic layer was washed with brine
  6. dry with materialdried over magnesium sulfate
  7. filtrationfiltered
  8. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-0d8a979212204b28b130bb2b161f8204
Source dataset
uspto-grants-1986_01
Patent number
US04567270

Reaction notes

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