Tert-butyl 3-[2-(2-hydroxymethylphenoxy)ethoxy]-4-{4-[3-(2-methoxybenzyloxy)propoxy]phenyl}piperidine-1-carboxylate → tert-Butyl 3-{2-[2-(2-hydroxypropoxymethyl)phenoxy]ethoxy}-4-{4-[3-(2-methoxybenzyloxy)propoxy]phenyl}piperidine-1-carboxylate

Participants

Reaction Steps

A solution of 0.34 g of tert-butyl 3-[2-(2-hydroxymethylphenoxy)ethoxy]-4-{4-[3-(2-methoxybenzyloxy)propoxy]phenyl}piperidine-1-carboxylate in 10 ml of N,N-dimethylformamide and 0.39 ml of (S)-(−)-propylene oxide (plus 0.3 ml after 2.5 hours, 1.0 ml after 5 hours) and one drop of 1,4-diazabicyclo[2.2.2]octane is stirred at 100° C. over 26 hours. The reaction mixture is cooled, diluted with 1N HCl and extracted with ethyl acetate (2×). The combined organic phases are dried over sodium sulphate and concentrated by evaporation. The title compound is obtained as a yellow oil from the residue by means of flash chromatography (SiO2 60F). Rf=0.38 (2:1 EtOAc-heptane); Rt=5.88.

Provenance & Evidence