Sodium hydride → 3-Bromo-1-t-butoxycarbonylmethyl-7-phenylperhydroazepin-2-one

Participants

Reaction Steps

A solution of 15.5 g of the lactam from Step A and 14.7 t-butyl iodoacetate in 150 ml tetrahydrofuran was added dropwise to a slurry of 1.45 g sodium hydride in 20 ml tetrahydrofuran. After 3 hr at room temperature the reaction was quenched by the addition of 15 ml sat. NH4Cl solution. The mixture was filtered and concentrated and the residue partitioned between CHCl3 and H2O. The crude product was obtained after drying and concentrating the CHCl3 solution. Chromatography over silica gel with hexane: ethyl acetate (4:1) afforded two isomers of 3-bromo-1-t-butoxycarbonylmethyl-7-phenylperhydroazepin-2-one: isomer A (minor, elutes first), and isomer B (major, elutes second).

Provenance & Evidence