4-(Trifluoromethyl)benzylamine → Ethyl 2-methyl-2-[2-methyl-4-({[4-(trifluoromethyl) benzyl]amino}methyl)phenoxy]propanoate

Participants

Reaction Steps

To a solution of ethyl 2-(4-formyl-2-methylphenoxy)-2-methylpropanoate (0.563 g, 2.25 mmol) in CH2Cl2 (10 mL) under nitrogen at room temperature, was added 4-trifluoromethylbenzyl amine (0.34 mL, 2.37 mmol). The resulting solution was stirred for 30 minutes prior to addition of sodium triacetoxyborohydride (0.668 g, 3.15 mmol). After 18 h stirring the reaction mixture was quenched by cautious addition of sat. sodium bicarbonate aq. (30 mL) and extracted CH2Cl2 (2×50 mL). The organic solution was dried (MgSO4) and the solvent removed in vacuo. Purification by SPE (Silica, 20 g) eluting 9:1 cyclohexane:EtOAc afforded the title compound as a colourless oil (0.485 g).

Provenance & Evidence