Triethylamine → 2-(4-Benzyl-4-hydroxy-piperidin-1-yl)-N-[4-(tert-butyl-dimethyl-silanyloxy)-phenyl)-acetamide

Participants

Reaction Steps

N-[4-(tert-Butyl-dimethyl-silanyloxy)-phenyl]-2-chloro-acetamide (1.14 g, 3.8 mmol) was dissolved in dimethylformamide (DMF) (12 ml) and stirred for 19 hours at room temperature in the presence of triethylamine (0.79 ml, 5.7 mmol) and 4-benzyl-4-hydroxypiperidin (0.87 g, 4.56 mmol). The reaction mixture was concentrated, dissolved in CH2Cl2 and washed with H2O (2×30 ml). The organic phase was dried over Na2SO4 and concentrated. The residue was chromatographed over silica gel (hexane-ethyl acetate 1:1 then ethyl acetate) to provide 2-(4-Benzyl-4-hydroxy-piperidin-1-yl)-N-[4-(tert-butyl-dimethyl-silanyloxy)-phenyl]-acetamide (1.32 g, 78%) as a yellow solid, m.p. 105°-108° C. and MS: m/e=455.5 (M+H+).

Provenance & Evidence