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

Participants

Reaction Conditions

Reaction Steps

trans-2-Benzyl-3a-methyl-6-((Z)-prop-1-enyl)-2,3,3a,4,5,9b-hexahydro-1H-benzo[e]isoindole (0.378 mmol, 120 mg) was dissolved in toluene (1 ml) and ACE-Cl (2.65 mmol, 291 μl) was added. The reaction mixture was heated to 160° C. for 15 minutes in a microwave reactor then MeOH (1 ml) was added. The reaction mixture was again heated in a microwave reactor at 160° C. for 5 minutes and the resulting solution was passed through an SCX cartridge and then purified by prep-HPLC. HCl in ether (1 ml) was added to the purified fractions before removal of solvent in vacuo to afford trans-3a-methyl-6-((Z)-prop-1-enyl)-2,3,3a,4,5,9b-hexahydro-1H-benzo[e]isoindole hydrochloride (13.6 mg), m/z: 228.1 [M+H]+.

Provenance & Evidence