Phenol → HCID 25156308, compound

Participants

Reaction Steps

To a solution of (+)-2-methyl-8-(pyridazin-3-yl)-2,3,4,5-tetrahydro-1H-benzo[c]azepin-5-ol (65 mg, 0.25) from Step A in THF (5 mL) was added phenol (73 mg, 0.77 mmol), tributylphosophine (156 mg, 0.77 mmol) and 1,1′-(azodicarboyl)dipiperidine (192 mg, 0.77 mmol) at room temperature. The reaction mixture was stirred at room temperature for 3 hours. The mixture was diluted with dichloromethane and washed with water, brine, dried over sodium sulfate and concentrated. The residue was purified by chromatography (98:2 to 95:5 ethyl acetate/methanol), followed by HPLC to give (−)-2-methyl-5-phenoxy-8-(pyridazin-3-yl)-2,3,4,5-tetrahydro-1H-benzo[c]azepine (52 mg, 62%) as a gum-like solid.

Provenance & Evidence