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)) stirring at 0° C. until the evolution of hydrogen had ceased at which time the reaction mixture was warmed to room temperature and stirred a further 1 hour. To the stirred reaction mixture was added dropwise a solution of 6 gm of t-butyl iodoacetate in 20 ml of THF stirring a further 2 hours at room temperature at which time the reaction was quenched with 20 ml of saturated NaHCO3. The reaction mixture was diluted with 20 ml of H2O and extracted 2×50 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. NMR (CDCl3, TMS) 1.4 (s, 9H); 2.0-3.2 (m, 4H), 3.4-3.8 (m, 1H); 4.6 (Q, 2H); 6.6-7.2 (m, 4H) IR C=O 1738, 1680

Provenance & Evidence