Potassium Carbonate → benzyl 4-(4-hydroxyphenyl)-3-[4-(3-methoxypropyl)-3-oxo-3,4-dihydro-2H-benzo[1,4]oxazin-6-ylmethoxy]piperidine-1-carboxylate

Participants

Reaction Steps

The solution of 10.0 g of benzyl 4-(4-allyloxyphenyl)-3-[4-(3-methoxypropyl)-3-oxo-3,4-dihydro-2H-benzo[1,4]oxazin-6-ylmethoxy]piperidine-1-carboxylate in 160 ml of methanol is admixed successively with 0.57 g of tetrakis(triphenylphosphine)palladium(0) and potassium carbonate. The reaction mixture is stirred at room temperature over 2 hours and subsequently concentrated by evaporation. The residue is admixed slowly with 2M HCl (70 ml) and extracted with dichloromethane (2×250 ml). The organic phases are washed with water (150 ml) and brine (150 ml), dried over sodium sulphate, filtered and concentrated by evaporation. The title compound is obtained as a colourless oil from the residue by means of flash chromatography (SiO2 60F). Rf=0.20 (3:2 EtOAc-heptane); Rt=4.54.

Provenance & Evidence