Cyclohexene → HCID 60068889, compound

HRID 392149Notes

Reaction equation

HRID 392149 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 hours 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. 1H NMR (CD3OD) δ 8.46 (m, 1H), 7.47 (m, 1H), 7.38-7.31 (m, 2H), 4.40 (m, 1H), 4.36 (m, 1H), 4.18 (m, 1H), 3.91 (m, 2H), 2.68 (s, 3H).

Workup

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

Sources & evidence

ORD record
ord-0462a2bfa0634519b60018a37148f475
Source dataset
uspto-grants-2004_10
Patent number
US06800637B2

Reaction notes

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