Cyclohexene → HCID 60068889, compound

HRID 720382Notes

Reaction equation

HRID 720382 reaction equation
C([O:8][CH2:9][CH:10]1[O:24][C:14]2=[C:15]3[C:20](=[CH:21][CH:22]=[C:13]2[O:12][CH2:11]1)[N:19]=[C:18]([CH3:23])[CH:17]=[CH:16]3)C1C=CC=CC=1.C1CCCCC=1>CCO.[Pd]>[CH3:23][C:18]1[CH:17]=[CH:16][C:15]2[C:20](=[CH:21][CH:22]=[C:13]3[O:12][CH2:11][C@@H:10]([CH2:9][OH:8])[O:24][C:14]3=2)[N:19]=1

Participants

5

Reactant 2

HCID 8079CyclohexeneHCID 22172756(Benzyloxy)methyl-8-methyl-2,3-dihydro[1,4]dioxino[2,3-f]quinoline

Product 1

HCID 60068889HCID 60068889, compoundYield 98%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

To a solution of (2S)-2[(benzyloxy)methyl-8-methyl-2,3-dihydro[1,4]dioxino [2,3-f]quinoline (0.16 g, 0.5 mmol) in EtOH (1 mL) was added cyclohexene (0.5 mL) then 10% Pd/C (0.016 g, 10 mol %). The mixture was heated to reflux under N2 for 18 h then cooled and filtered. The catalyst was rinsed with methanol and the filtrate was concentrated in vacuo to afford 0.113 g (98%) of the title alcohol as an off-white solid.

Workup

  1. temperatureThe mixture was heated
  2. temperatureto reflux under N2 for 18 h
  3. temperaturethen cooled
  4. filtrationfiltered
  5. washThe catalyst was rinsed with methanol
  6. concentrationthe filtrate was concentrated in vacuo

Sources & evidence

ORD record
ord-182c10f386f04b77a5a07597be64944b
Source dataset
uspto-grants-2006_11
Patent number
US07135479B2

Reaction notes

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