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

Participants

Reaction Steps

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]+.

Provenance & Evidence