Pyridine → HCID 86638053, compound

Participants

Reaction Steps

To a solution of 1-[8-hydroxy-3-(trifluoroacetyl)-2,3,4,5-tetrahydro-1H-3-benzazepin-7-yl]ethanone (7.4 mmol) in pyridine (15 ml) hydroxylamine hydrochloride (8.9 mmol) was added at room temperature and the reaction mixture was stirred for 4 h. Solvent was removed under reduced pressure, the residue was partitioned between 10% aqueous Na2CO3 and EtOAc. The organic layer was collected and the aqueous phase extracted twice with EtOAc. The combined organic layers were concentrated and the resulting material was dissolved in THF (5 ml) and Ph3P (15 mmol) was added. The reaction mixture was stirred at 50° C. for 10 min while DEAD (15 mmol, 40% in toluene) was slowly added. The reaction mixture was stirred at 50° C. for 15 min then cooled to room temperature and water (0.4 ml) was added. Solvent was removed under reduced pressure and the residue was submitted to column chromatography to provide 3-methyl-7-(trifluoroacetyl)-6,7,8,9-tetrahydro-5H-isoxazolo[4,5-h][3]benzazepine (NMR 1H, CDCl3): δ 7.4-7.3 (m, 2H), 3.85-3.65 (m, 4H), 3.15-3.05 (m, 4H), 2.55 (s, 3H). MS (m/z): 299 [MH]+). Treatment with K2CO3 (4 eq) in MeOH:H2O (1:1) gave the title compound (1.3 mmol) as pale yellow oil, which was used without further characterisation.

Provenance & Evidence