Acetic Acid → 4-({[4-(Tert-butyl-dimethyl-silanyloxy)-2-methyl-phenyl]-methyl-amino}-methyl)-2-methyl-benzoic acid methyl ester

Participants

Reaction Steps

A mixture of [4-(tert-butyl-dimethyl-silanyloxy)-2-methyl-phenyl]-methyl-amine (643 mg, 2.6 mmol, 1.2 eq) and 4-formyl-2-methyl-benzoic acid methyl ester (380 mg, 2.1 mmol), acetic acid (252 mg, 4.2 mmol, 2.0 eq.), sodium triacetoxyborohydride (890 mg, 4.2 mmol, 2.0 eq.) in 1,2-dichloroethane is stirred at room temperature overnight. The mixture is concentrated under reduced pressure and the resulting residue is partitioned between EtOAc (50 mL) and 5% NaHCO3 (40 mL). The organic. phase is washed with brine (50 mL), dried (Na2SO4), filtered, and concentrated under reduced pressure to a residue. The residue is purified by flash chromatography eluting with a gradient of EtOAc/Hexane to afford the title compound as a syrup (1.0 g, 95%). LC-ES/MS m/e 414.3 (M+1).

Provenance & Evidence