Sodium hydride → HCID 14590305, compound

Participants

Reaction Steps

To a suspension of 2.42 gm NaH (50% oil dispersion washed 3×hexanes) in 50 ml of THF at 0° C. was added solid 5 gm (0.025 mol) of 3-aminodihydrocarbostyrilhydrochloride (T. J. McCord, Arch. of Biochem. & Biophys. 102 48, 1963) and the mixture was stirred at 0° C. until the evolution of hydrogen had ceased. When the evolution stopped, the reaction mixture was warmed to room temperature and stirred an additional 1 hour, at which time a solution of 6 gm of t-butyl iodoacetate in 20 ml of THF was added dropwise. After an additional two hours of stirring at room temperature, the reaction was quenched with 20 ml of saturated NaHCO3, and the reaction mixture was diluted with 20 ml of H2O and extracted twice with 50 ml of 9:1 ethylacetate:acetonitrile. The organic layers were combined, filtered through MgSO4 and concentrated in vacuo to give 5 gm of 1-t-butoxycarbonylmethyl-3 -aminodihydrocarbostyril.

Provenance & Evidence