Acetic Acid → {[4-(tert-Butyl-dimethyl-silanyloxy)-2-methyl-phenyl]-methyl-amino}-methyl-2-methyl-benzoic Acid Methyl Ester

Participants

Reaction Steps

To a solution of [4-(tert-butyl-dimethyl-silanyloxy)-2-methyl-phenyl]-methyl-amine (0.64 g, 2.6 mmol) and 4-formyl-2-methyl-benzoic acid methyl ester (0.38 g, 2.1 mmol), acetic acid (0.25 g, 4.2 mmol) in 1,2-dichloroethane (10.0 mL) is added sodium triacetoxyborohydride (0.89 g, 4.2 mmol) in portions. The mixture is stirred at room temperature overnight. The reaction is quenched with 5% aq. sodium bicarbonate (5 mL) and is partitioned between EtOAc (60 mL) and water (50 mL). The organic layer is washed with brine (50 mL), dried (Na2SO4), filtered, and concentrated. The residue is purified by flash column chromatography to afford the title compound as a syrup (1.0 g, 95%). LC-ES/MS m/e 414.3 (M+1).

Provenance & Evidence