Acetic Acid → HCID 66988160, compound

HRID 333438Notes

Reaction equation

HRID 333438 reaction equation
[C:1]1([C:7]2([C:20](=[O:23])[CH2:21][CH3:22])[CH2:12][CH2:11][N:10]([C:13]([O:15][C:16]([CH3:19])([CH3:18])[CH3:17])=[O:14])[CH2:9][CH2:8]2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.C(O)(=O)C>O1CCOCC1.[Rh]>[CH:1]1([C:7]2([C:20](=[O:23])[CH2:21][CH3:22])[CH2:8][CH2:9][N:10]([C:13]([O:15][C:16]([CH3:18])([CH3:19])[CH3:17])=[O:14])[CH2:11][CH2:12]2)[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6]1

Participants

5

Reactant 2

HCID 176Acetic AcidHCID 66987988HCID 66987988, compound

Product 1

HCID 66988160HCID 66988160, compoundYield 93%

Reagents, catalysts & solvents 2

HCID 23948RhodiumCatalystHCID 312751,4-DioxaneSolvent

Conditions

Temperature
80 °C

Procedure

The following are introduced into a Parr bomb: 582 mg (1.83 mmol) of tert-butyl 4-phenyl-4-propionylpiperidine-1-carboxylate, 300 mg of rhodium on alumina and 0.5 mL of acetic acid in 15 mL of dioxane. The reaction mixture is placed under a hydrogen pressure of 6 bar and stirred at 80° C. for 16 hours. The reaction is stopped, filtered through Celite and washed with dichloromethane. The solvents are evaporated off and the residue is then chromatographed on silica gel (eluent: 95/5 heptane/ethyl acetate). 549 mg of tert-butyl 4-cyclohexyl-4-propionylpiperidine-1-carboxylate in the form of a colourless oil are obtained in a yield of 93%.

Workup

  1. additionThe following are introduced into a Parr bomb
  2. filtrationfiltered through Celite
  3. washwashed with dichloromethane
  4. customThe solvents are evaporated off
  5. customthe residue is then chromatographed on silica gel (eluent: 95/5 heptane/ethyl acetate)

Sources & evidence

ORD record
ord-1122e82bef014603b5cca50eb0fce927
Source dataset
uspto-grants-2014_11
Patent number
US08877968B2

Reaction notes

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