Acetic Acid → 2-[(Benzylamino)methyl]-5-tert-butylphenol

Participants

Reaction Steps

To a mixture of 0.216 g (1.0 mmol) of the product of Example 1 and 0.108 g (0.1 mmol) of benzaldehyde suspended in 5 mL of 1,2-dichloroethane was added 0.5 mL acetic acid and 1 g of finely powdered 4 Å molecular sieves. The reaction mixture was stirred under a nitrogen atmosphere at room temperature overnight, then 1.12 g (5 mmol) of sodium triacetoxyborohydride was added. The reaction was then stirred an addition day at room temperature, then diluted with CH2Cl2 and MeOH. The mixture was filtered through a pad of Celite filter aid eluted with CH2Cl2, and the filtrate was washed with saturated aq. NaHCO3. The organic layer was the separated, dried (Na2SO4), filtered and evaporated in vacuo. The residue was purified on a flash chromatography column eluted with CH2Cl2-MeOH—NH4HO (97:2:1) to afford the title compound.

Provenance & Evidence