Cyclohexene → Ethyl 4-(4-hydroxy-2-oxopyridin-1(2H)-yl)-2-methyl-2-(methylsulfonyl)butanoate

HRID 1475903Notes

Reaction equation

HRID 1475903 reaction equation
C([O:8][C:9]1[CH:14]=[CH:13][N:12]([CH2:15][CH2:16][C:17]([CH3:27])([S:23]([CH3:26])(=[O:25])=[O:24])[C:18]([O:20][CH2:21][CH3:22])=[O:19])[C:11](=[O:28])[CH:10]=1)C1C=CC=CC=1.C1CCCCC=1>C(O)C.[OH-].[OH-].[Pd+2]>[OH:8][C:9]1[CH:14]=[CH:13][N:12]([CH2:15][CH2:16][C:17]([CH3:27])([S:23]([CH3:26])(=[O:25])=[O:24])[C:18]([O:20][CH2:21][CH3:22])=[O:19])[C:11](=[O:28])[CH:10]=1

Participants

5

Reactant 2

HCID 8079CyclohexeneHCID 67249611Ethyl 4-(4-(benzyloxy)-2-oxopyridin-1(2h)-yl)-2-methyl-2-(methylsulfonyl)butanoate

Product 1

HCID 67248478Ethyl 4-(4-hydroxy-2-oxopyridin-1(2H)-yl)-2-methyl-2-(methylsulfonyl)butanoate

Reagents, catalysts & solvents 2

HCID 9942167Palladium hydroxideCatalystHCID 702EthanolSolvent

Conditions

Temperature
85 °C

Procedure

Ethyl 4-[4-(benzyloxy)-2-oxopyridin-1(2H)-yl]-2-methyl-2-(methylsulfonyl)butanoate (2.4 g, 5.9 mmol) which may be prepared by the same method disclosed in Example 51, step A, was dissolved in ethanol (100 ml) and cooled with a dry ice/acetone bath. To the cooled solution was added Pearlman's catalyst (2.0 g) and cyclohexene (9.0 ml, 88.4 mmol) then heated to 85° C. for 3 hours. The reaction mixture was cooled to RT and filtered through celite (approx 2 inches) to remove catalyst. The celite was washed with an additional 100 ml of ethanol. The filtrate was then concentrated under reduced pressure and the residue was dried under vacuum to afford a light gray solid. (1.75 g, 94%). MS (LC/MS) m/z 318.1 (M+1) 1H NMR (400 MHz, DMSO-d6) δ ppm 1.22 (t, J=7.02 Hz, 3H) 1.56 (s, 3H) 2.02-2.26 (m, 1H) 2.33-2.48 (m, 1H) 3.14 (s, 3H) 3.67-3.84 (m, 1H) 3.84-4.02 (m, 1H) 4.13 (dd, J=7.02, 4.49 Hz, 2H) 5.55 (d, J=2.54 Hz, 1H) 5.85 (dd, J=7.42, 2.54 Hz, 1H) 7.48 (d, J=7.42 Hz, 1H)

Workup

  1. temperaturecooled with a dry ice/acetone bath
  2. temperatureThe reaction mixture was cooled to RT
  3. filtrationfiltered through celite (approx 2 inches)
  4. customto remove catalyst
  5. washThe celite was washed with an additional 100 ml of ethanol
  6. concentrationThe filtrate was then concentrated under reduced pressure
  7. customthe residue was dried under vacuum
  8. customto afford a light gray solid

Sources & evidence

ORD record
ord-7c3a4bc267584494b2193357604eb686
Source dataset
uspto-grants-2015_04
Patent number
US09018384B2

Reaction notes

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