Cyclohexene → Ethyl 4-{3-methoxy-4-[3-(pyridin-2-ylamino)propoxy]phenyl}-3,3-dimethylbutanoate

HRID 1860678Notes

Reaction equation

HRID 1860678 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[C:5]([CH2:21][C:22]([CH3:30])([CH3:29])[CH2:23][C:24]([O:26][CH2:27][CH3:28])=[O:25])[CH:6]=[CH:7][C:8]=1[O:9][CH2:10][CH2:11][CH2:12][NH:13][C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][N+:15]=1[O-].C1CCCCC=1>[Pd].CC(O)C>[CH3:1][O:2][C:3]1[CH:4]=[C:5]([CH2:21][C:22]([CH3:29])([CH3:30])[CH2:23][C:24]([O:26][CH2:27][CH3:28])=[O:25])[CH:6]=[CH:7][C:8]=1[O:9][CH2:10][CH2:11][CH2:12][NH:13][C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][N:15]=1

Participants

5

Reactant 2

HCID 8079CyclohexeneHCID 178471327HCID 178471327, compound

Product 1

HCID 12018742Ethyl 4-{3-methoxy-4-[3-(pyridin-2-ylamino)propoxy]phenyl}-3,3-dimethylbutanoateYield 84.3%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 3776IsopropanolSolvent

Procedure

A mixture of the product of STEP 7 (81.5 mg, 0.2mmol), 10% Pd/C (50 mg, 0.05 mmol), cyclohexene (0.5 ml, 4.9 mmol), and 2-propanol (5 ml) was heated at reflux for 3 h. The reaction was cooled to room temperature, filtered through a short column of Celite®, and washed with 2-propanol. The filtrate was concentrated to give 67.5 mg pale brown oil. The NMR spectra were consistent for the proposed structure.

Workup

  1. temperaturewas heated
  2. temperatureat reflux for 3 h
  3. filtrationfiltered through a short column of Celite®
  4. washwashed with 2-propanol
  5. concentrationThe filtrate was concentrated

Sources & evidence

ORD record
ord-d0c4dcef0d244ef8b133ec400e24e4aa
Source dataset
uspto-grants-2003_03
Patent number
US06531494B1

Reaction notes

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