4-(2-Acetamidopropan-2-yl)benzoic acid → Methyl 4-(1-acetamido-1-methylethyl)cyclohexanecarboxylate

HRID 2260567Notes

Reaction equation

HRID 2260567 reaction equation
[C:1]([NH:4][C:5]([C:8]1[CH:16]=[CH:15][C:11]([C:12]([OH:14])=[O:13])=[CH:10][CH:9]=1)([CH3:7])[CH3:6])(=[O:3])[CH3:2].[H][H].[C:19](NC(C1CCC(C(O)=O)CC1)(C)C)(=O)C.Cl.CO>N.[C].[Ru].CO>[C:1]([NH:4][C:5]([CH:8]1[CH2:9][CH2:10][CH:11]([C:12]([O:14][CH3:19])=[O:13])[CH2:15][CH2:16]1)([CH3:7])[CH3:6])(=[O:3])[CH3:2]

Participants

8

Reactant 4

HCID 184231434-(2-Acetamidopropan-2-yl)benzoic acidHCID 189985724-(1-Acetamido-1-methylethyl)cyclohexanecarboxylic acidHCID 21893726Hydrochloride methanolHCID 178418361HCID 178418361, compound

Product 1

HCID 18998535Methyl 4-(1-acetamido-1-methylethyl)cyclohexanecarboxylate

Reagents, catalysts & solvents 3

HCID 178503044HCID 178503044, compoundCatalystHCID 222AmmoniaSolventHCID 887MethanolSolvent

Procedure

A solution (200 ml) of 4-(1-acetamido-1-methylethyl)benzoic acid (17.9 g) and 5% ruthenium carbon (60 g) in 10% aqueous ammonia was stirred in an autoclave at initial hydrogen pressure of 70 atm and at 150°-170° C. for 3 hours. After completion of the reaction, the catalyst was filtered off and the filtrate was concentrated under reduced pressure to give a cis- and trans- mixture of 4-(1-acetamido-1-methylethyl)cyclohexanecarboxylic acid. Then, 31% hydrochloric acid-methanol (15 ml ) and methanol (100 ml ) were added thereto and the mixture was refluxed for 4 hours. After completion of the reaction, the mixture was concentrated under reduced pressure and the residue was extracted with chloroform. The extract was washed with water, dried and concentrated under reduced pressure. The residue obtained was purified by silica gel column chromatography to give 14.0 g of a cis- and trans-mixture (3:1) of methyl 4-(1-acetamido-1-methylethyl)cyclohexanecarboxylate.

Workup

  1. customAfter completion of the reaction
  2. filtrationthe catalyst was filtered off
  3. concentrationthe filtrate was concentrated under reduced pressure
  4. customto give
  5. temperaturethe mixture was refluxed for 4 hours
  6. customAfter completion of the reaction
  7. concentrationthe mixture was concentrated under reduced pressure
  8. extractionthe residue was extracted with chloroform
  9. washThe extract was washed with water
  10. customdried
  11. concentrationconcentrated under reduced pressure
  12. customThe residue obtained
  13. customwas purified by silica gel column chromatography

Sources & evidence

ORD record
ord-21f2fdd97d91435898c6f7948a0bcfdc
Source dataset
uspto-grants-1995_12
Patent number
US05478838

Reaction notes

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