Tetrabutylammonium Fluoride → HCID 68502906, compound

Participants

Reaction Steps

To the solution of the (−)-5-(tert-butyldimethylsilyloxy)-2-methyl-8-(pyridazin-3-yl)-2,3,4,5-tetrahydro-1H-benzo[c]azepine (2.14 g, 5.8 mmol) from Step G above in THF was added TBAF (1.0 M in THF, 10 mL, 10 mmol). The reaction mixture was stirred at room temperature for 3 hours. The solvent was removed. The residue was purified by flash chromatography (97:2.7:0.3 to 93:6.3:0.7 ethyl acetate/methanol/concentrated ammonium hydroxide) to give (−)-2-methyl-8-(pyridazin-3-yl)-2,3,4,5-tetrahydro-1H-benzo[c]azepin-5-ol (1.34 g, 90%) as a white solid ([α]25D, −28.6°, (C, 0.18 Methanol)): ESI MS m/z 256 [M+H]+.

Provenance & Evidence