Acetone → HCID 45262213, compound

HRID 1614823Notes

Reaction equation

HRID 1614823 reaction equation
[ClH:1].[CH3:2][C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][C:4]=1[C:9]([C:24]1[CH:29]=[CH:28][CH:27]=[CH:26][C:25]=1[CH3:30])=[CH:10][CH2:11][O:12][CH2:13][CH2:14][N:15]1[CH2:20][CH2:19][CH2:18][C@@H:17]([C:21]([OH:23])=[O:22])[CH2:16]1.C(OCC)(=O)C.CC(C)=O>CO.[Pd]>[ClH:1].[CH3:30][C:25]1[CH:26]=[CH:27][CH:28]=[CH:29][C:24]=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][N:15]1[CH2:20][CH2:19][CH2:18][C@@H:17]([C:21]([OH:23])=[O:22])[CH2:16]1

Participants

6

Reactant 3

HCID 180AcetoneHCID 8857Ethyl AcetateHCID 45265069HCID 45265069, compound

Product 1

HCID 45262213HCID 45262213, compoundYield 67%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

The acid prepared in Example 29 (1.1 g, 2.6 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 a mixture of methanol and toluene to give 0.75 g (67%) 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 a mixture of methanol and toluene

Sources & evidence

ORD record
ord-c2b23b4741584f4fa08a9c2aad0c9a96
Source dataset
uspto-grants-1993_03
Patent number
US05198451

Reaction notes

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