Methanol → cis-3a-Methyl-6-((Z)-prop-1-enyl)-2,3,3a,4,5,9b-hexahydro-1H-benzo[e]isoindole hydrochloride

Participants

Reaction Conditions

Reaction Steps

cis-2-Benzyl-3a-methyl-6-((Z)-prop-1-enyl)-2,3,3a,4,5,9b-hexahydro-1H-benzo[e]isoindole (0.372 mmol, 118 mg) was dissolved in toluene (1 ml) and ACE-Cl (2.60 mmol, 0.286 ml, 372 mg) was added. The reaction mixture was heated to 160° C. for 15 minutes and then MeOH (1 ml) was added and the reaction mixture was heated to 160° C. for a further 5 minutes and then passed through an SCX cartridge and the resulting filtrate was purified by silica column chromatography (eluting with DCM—2, 4, 8, 16% MeOH(NH3)/DCM) The pure fractions were concentrated in vacuo and then 2 N HCl in MeOH added. The resulting solution was concentrated in vacuo to afford cis-3a-methyl-6-((Z)-prop-1-enyl)-2,3,3a,4,5,9b-hexahydro-1H-benzo[e]isoindole hydrochloride (85 mg): m/z: 228.1 [M+H]+.

Provenance & Evidence