Cyclohexene → HCID 9949120, compound

HRID 989041Notes

Reaction equation

HRID 989041 reaction equation
C([N:11]1[CH2:34][CH2:33][N:14]2[C:15]3[C:20]([NH:21][C:22](=[O:23])[CH:13]2[CH2:12]1)=[CH:19][C:18]([C:24]1[CH:29]=[CH:28][C:27]([O:30][CH3:31])=[CH:26][C:25]=1[CH3:32])=[CH:17][CH:16]=3)(OCC1C=CC=CC=1)=O.C1CCCCC=1>C(O)C.[Pd]>[CH3:31][O:30][C:27]1[CH:28]=[CH:29][C:24]([C:18]2[CH:19]=[C:20]3[C:15](=[CH:16][CH:17]=2)[N:14]2[CH2:33][CH2:34][NH:11][CH2:12][CH:13]2[C:22](=[O:23])[NH:21]3)=[C:25]([CH3:32])[CH:26]=1

Participants

5

Reactant 2

HCID 8079CyclohexeneHCID 12109646HCID 12109646, compound

Product 1

HCID 9949120HCID 9949120, compoundYield 24.4%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

Deprotection procedure: To a solution of 3-carbobenzyloxy-8-(4-methoxy-2-methylpheny)-2,3,4, 4a-tetrahydro-1H-pyrazino [1,2-a]quinoxalin-5(6H) -one (0.38 mmol) in 6 ml absolute ethanol was added 10% Pd/C (150 mg) and excess cyclohexene (3 ml). The black reaction mixture was heated to reflux. After 5 h, the mixture was cooled to rt and filtered through a pad of celite, washing heavily with methanol. The filtrate was concentrated to a colorless residue. The crude material was purified by radial PLC (1 mm plate, load and elute with methanol) to give the title compound as a colorless oil (30 mg, 24%). 1H NMR (CDCl3, 300 MHz) δ7.12 (d, J=8.1 Hz, 1H), 6.95 (dd, J=8.5, 1.9 Hz, 1H), 6.76-6.82 (m, 3H), 6.67 (d, J=1.8 Hz, 1H), 3.83 (s, 3H), 3.53-3.67 (m, 3H), 3.18 (m, 1H), 2.79-3.01 (m, 3H), 2.26 (s, 3H) ppm. MS (ESI) m/z=324.2 [M+H]+.

Workup

  1. customThe black reaction mixture
  2. temperaturewas heated to reflux
  3. filtrationfiltered through a pad of celite
  4. washwashing heavily with methanol
  5. concentrationThe filtrate was concentrated to a colorless residue
  6. customThe crude material was purified by radial PLC (1 mm plate, load and elute with methanol)

Sources & evidence

ORD record
ord-23a79ef503774b78a6941dc7651c4bb4
Source dataset
uspto-grants-2003_10
Patent number
US06638934B2

Reaction notes

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