Sodium hydride → HCID 68574727, compound

Participants

Reaction Conditions

Reaction Steps

1.61 g of sodium hydride dispersion (60%) are added to a solution of 19.76 g of benzyl 4-(4-allyloxyphenyl)-3-hydroxy-5 -triisopropylsilanyloxypiperidine-1-carboxylate and 9.95 g of 6-chloromethyl-4-(3-methoxypropyl)-4H-benz[1,4]-oxazin-3-one in 285 ml of N,N-dimethylformamide while the reaction mixture is stirred at 10° C. for 1 hour and at room temperature for 18 hours. The mixture is poured into 1M aqueous sodium bicarbonate solution (700 ml) and extracted with tert-butyl methyl ether 2×800 ml). The organic phases are washed successively with water (2×500 ml) and brine (1×500 ml), dried with sodium sulphate and evaporated. The title compound is obtained from the residue by flash chromatography (SiO260 F). Rf (EtOAc/heptane 2:3)=0.30, Rt=7.15.

Provenance & Evidence