trans-3a-Methyl-6-(prop-1-en-2-yl)-2,3,3a,4,5,9b-hexahydro-1H-benzo[e]isoindole hydrochloride → trans-6-Isopropyl-3a-methyl-2,3,3a,4,5,9b-hexahydro-1H-benzo[e]isoindole hydrochloride

HRID 1026646Notes

Reaction equation

HRID 1026646 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]([C:16]([CH3:18])=[CH2:17])[C:6]=1[CH2:5][CH2:4]2>C(O)C.C(O)(=O)C.[Pd]>[ClH:1].[CH:16]([C:15]1[C:6]2[CH2:5][CH2:4][C@@:3]3([CH3:2])[C@@H:8]([CH2:9][NH:10][CH2:11]3)[C:7]=2[CH:12]=[CH:13][CH:14]=1)([CH3:18])[CH3:17]

Participants

5

Reactant 1

HCID 70664562trans-3a-Methyl-6-(prop-1-en-2-yl)-2,3,3a,4,5,9b-hexahydro-1H-benzo[e]isoindole hydrochloride

Product 1

HCID 70664699trans-6-Isopropyl-3a-methyl-2,3,3a,4,5,9b-hexahydro-1H-benzo[e]isoindole hydrochlorideYield 118.1%

Reagents, catalysts & solvents 3

HCID 23938PalladiumCatalystHCID 176Acetic AcidSolventHCID 702EthanolSolvent

Procedure

trans-3a-Methyl-6-(prop-1-en-2-yl)-2,3,3a,4,5,9b-hexahydro-1H-benzo[e]isoindole hydrochloride (41 mg, 0.137 mmol) was dissolved in ethanol (2 ml) and acetic acid (0.5 ml). 5% Pd on C (0.298 mg) was added and the reaction mixture was stirred under an atmosphere of H2 (1 bar) for 18 h. The resulting suspension was filtered through celite and then passed through an SCX cartridge. The purified fractions were concentrated in vacuo and then dissolved in DCM (1 ml). 2 N HCl in Et2O (1 ml) was added and the solvent was removed in vacuo to afford trans-6-Isopropyl-3a-methyl-2,3,3a,4,5,9b-hexahydro-1H-benzo[e]isoindole hydrochloride (43 mg), m/z: 230.3 [M+H]+.

Workup

  1. filtrationThe resulting suspension was filtered through celite
  2. concentrationThe purified fractions were concentrated in vacuo
  3. dissolutiondissolved in DCM (1 ml)
  4. addition2 N HCl in Et2O (1 ml) was added
  5. customthe solvent was removed in vacuo

Sources & evidence

ORD record
ord-06ae8a6497044552adeff51fd7c17baa
Source dataset
uspto-grants-2014_05
Patent number
US08729274B2

Reaction notes

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