Aluminium lithium hydride → HCID 178457505, compound

Participants

Reaction Steps

Lithium aluminum hydride (70 mg, 1.84 mmol) was added to a tetrahydrofuran solution (5 ml) of the cis-N-{4-[(4,7-dimethyl-1H-indazol-5-yl)oxy]cyclohexyl}propanamide (116 mg, 0.368 mmol) obtained in Example 668, and the resulting mixture was heated under reflux for 5 hours. After the reaction solution was diluted with 10 ml of tetrahydrofuran, the reaction was terminated by careful addition of water (76 μl), a 4N-aqueous sodium hydroxide solution (76 μl) and water (230 μl) in that order under ice-cooling. The reaction solution thus treated was filtered by the use of Celite and the solvent was distilled off under reduced pressure to obtain a crude product. The crude product was purified by a preparative thin-layer silica gel chromatography (chloroform/methanol/aqueous ammonia=7:1:0.1) to obtain cis-N-{4-[(4,7-dimethyl-1H-indazol-5-yl)oxy]cyclohexyl}-N-propylamine (64 mg, 58%).

Provenance & Evidence