Acetic Acid → Ethyl acetate methanol ammonium hydroxide

Participants

Reaction Steps

[2-(5-Methoxy-benzoimidazol-1-yl)-quinolin-8-yloxy]-acetaldehyde 135A (214 mg, 064 mMol), 400 μL of AcOH, 1.6 mL of a solution of 2 M methylamine in MeOH and Na(OAc)3BH (204, 0.96 mMol) were added to 3 mL of DCE under an atmosphere of dry N2. The reaction mixture was stirred overnight at ambient temperature after which time it was partitioned between DCM and aqueous 1 N NaOH. The DCM layer was washed 2 more times with aqueous 1 N NaOH, then with brine, dried over Na2SO4, filtered and concentrated under vacuum. The resulting residue was chromatographed on flash silica gel initially eluting with MeOH/EtOAc (4:96), then MeOH/EtOAc/NH4OH (8:91.9:0.1), then MeOH/EtOAc/NH4OH (10:89.9:0.1) and finally MeOH/EtOAc/NH4OH (15:84.9:0.1) to give 28 mg of the title compound 135 as a white solid.

Provenance & Evidence