Cyclohexene → HCID 9949120, compound

Participants

Reaction Steps

Deprotection procedure: To a solution of 3-carbobenzyloxy-8-(4-methoxy-2-methylpheny)-2,3,4, 4a-tetrahydro-1H-pyrazino [1,2-a]quinoxalin-5(6H) -one (0.38 mmol) in 6 ml absolute ethanol was added 10% Pd/C (150 mg) and excess cyclohexene (3 ml). The black reaction mixture was heated to reflux. After 5 h, the mixture was cooled to rt and filtered through a pad of celite, washing heavily with methanol. The filtrate was concentrated to a colorless residue. The crude material was purified by radial PLC (1 mm plate, load and elute with methanol) to give the title compound as a colorless oil (30 mg, 24%). 1H NMR (CDCl3, 300 MHz) δ7.12 (d, J=8.1 Hz, 1H), 6.95 (dd, J=8.5, 1.9 Hz, 1H), 6.76-6.82 (m, 3H), 6.67 (d, J=1.8 Hz, 1H), 3.83 (s, 3H), 3.53-3.67 (m, 3H), 3.18 (m, 1H), 2.79-3.01 (m, 3H), 2.26 (s, 3H) ppm. MS (ESI) m/z=324.2 [M+H]+.

Provenance & Evidence