Acetic Acid → cis-3a-methyl-6-propyl-2,3,3a,4,5,9b-hexahydro-1H-benzo[e]isoindole hydrochloride

HRID 1026631Notes

Reaction equation

HRID 1026631 reaction equation
[ClH:1].[CH3:2][C@@:3]12[CH2:11][NH:10][CH2:9][C@@H:8]1[C:7]1[CH:12]=[CH:13][CH:14]=[C:15](/[CH:16]=[CH:17]\[CH3:18])[C:6]=1[CH2:5][CH2:4]2.C(O)(=O)C>CCO.[Pd]>[ClH:1].[CH3:2][C@@:3]12[CH2:11][NH:10][CH2:9][C@@H:8]1[C:7]1[CH:12]=[CH:13][CH:14]=[C:15]([CH2:16][CH2:17][CH3:18])[C:6]=1[CH2:5][CH2:4]2

Participants

5

Reactant 2

HCID 176Acetic AcidHCID 70664554cis-3a-Methyl-6-((Z)-prop-1-enyl)-2,3,3a,4,5,9b-hexahydro-1H-benzo[e]isoindole hydrochloride

Product 1

HCID 70664385cis-3a-methyl-6-propyl-2,3,3a,4,5,9b-hexahydro-1H-benzo[e]isoindole hydrochlorideYield 28.9%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalyst2×HCID 702EthanolSolvent

Procedure

cis-3a-Methyl-6-((Z)-prop-1-enyl)-2,3,3a,4,5,9b-hexahydro-1H-benzo[e]isoindole hydrochloride (0.352 mmol, 80 mg) was dissolved in EtOH (2 ml) and palladium (5% on carbon) (0.035 mmol, 3.74 mg) was added. The resulting suspension was stirred under an atmosphere of hydrogen (balloon) for 72 h. Acetic acid (1 ml) and further palladium (5% on carbon) (0.035 mmol, 3.74 mg) was added and the reaction mixture left to stir for further 2 hours and then filtered through dicalite. The filtrate was concentrated in vacuo and the resulting crude residue was passed through an SCX cartridge and then purified by silica column chromatography (eluting with DCM—16% (2 N NH3 in MeOH)/DCM)). The pure fractions were concentrated in vacuo and then dissolved in DCM (1 ml) and 2N HCl in ether added. The resulting solution was concentrated in vacuo to afford cis-3a-methyl-6-propyl-2,3,3a,4,5,9b-hexahydro-1H-benzo[e]isoindole hydrochloride 27 mg. m/z: 230.1 [M+H]+.

Workup

  1. waitthe reaction mixture left
  2. stirringto stir for further 2 hours
  3. filtrationfiltered through dicalite
  4. concentrationThe filtrate was concentrated in vacuo
  5. custompurified by silica column chromatography (eluting with DCM—16% (2 N NH3 in MeOH)/DCM))
  6. concentrationThe pure fractions were concentrated in vacuo
  7. dissolutiondissolved in DCM (1 ml)
  8. addition2N HCl in ether added
  9. concentrationThe resulting solution was concentrated in vacuo

Sources & evidence

ORD record
ord-5a1ae8402cfe453a88ff540bc927440d
Source dataset
uspto-grants-2014_05
Patent number
US08729274B2

Reaction notes

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