Acetone → HCID 70231090, compound

HRID 566553Notes

Reaction equation

HRID 566553 reaction equation
[ClH:1].[CH3:2][C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][C:4]=1[C:9]([C:25]1[CH:30]=[CH:29][CH:28]=[CH:27][C:26]=1[CH3:31])=[CH:10][CH2:11][O:12][CH2:13][CH2:14][CH2:15][N:16]1[CH2:21][CH2:20][CH2:19][C@@H:18]([C:22]([OH:24])=[O:23])[CH2:17]1.C(OCC)(=O)C.CC(C)=O>CO.[Pd]>[ClH:1].[CH3:31][C:26]1[CH:27]=[CH:28][CH:29]=[CH:30][C:25]=1[CH:9]([C:4]1[CH:5]=[CH:6][CH:7]=[CH:8][C:3]=1[CH3:2])[CH2:10][CH2:11][O:12][CH2:13][CH2:14][CH2:15][N:16]1[CH2:21][CH2:20][CH2:19][C@@H:18]([C:22]([OH:24])=[O:23])[CH2:17]1

Participants

6

Reactant 3

HCID 180AcetoneHCID 8857Ethyl AcetateHCID 45262100HCID 45262100, compound

Product 1

HCID 70231090HCID 70231090, compoundYield 26.4%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

The acid prepared in Example 34 (0.75 g, 1.7 mmol) was dissolved in methanol (25 ml) and stirred under an atmosphere of hydrogen for 1 h at room temperature in the presence of 10% palladium on carbon catalyst (35% aqueous paste) and then filtered. The filtrate was evaporated to dryness leaving a residue which was treated with a mixture of ethyl acetate and acetone and filtered to give a solid which was recrystallised from toluene to give 0.20 g (26%) of the title compound as a solid.

Workup

  1. filtrationfiltered
  2. customThe filtrate was evaporated to dryness
  3. customleaving a residue which
  4. filtrationfiltered
  5. customto give a solid which
  6. customwas recrystallised from toluene

Sources & evidence

ORD record
ord-f079eca4e79c4fbdb4dca6f3b010d219
Source dataset
uspto-grants-2001_01
Patent number
US06174898B1

Reaction notes

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