Hydrochloric Acid → HCID 21349882, compound

Participants

Reaction Conditions

Reaction Steps

4-(3-(2-naphthoylamino)propyl)-3-oxo-8-(tetrahydropyran-2-yloxy)-3,4-dihydro-2H-1,4-benzooxazine (398 mg) was dissolved in methanol (5 ml), and a 1N hydrochloric acid aqueous solution was added to the resultant solution, and the mixture was stirred at 0° C. for 1 hour. The reaction solution was extracted with ethyl acetate, and the resultant organic layer was washed with saturated brine, and then dried over anhydrous sodium sulfate. The solvent was distilled off under reduced pressure, and the resultant residue was dissolved in THF (5 ml). A borane THF complex (1.0 M in THF, 2.8 ml) was added to the resultant solution, and then the mixture was refluxed under heating for 3.5 hours. A saturated sodium bicarbonate aqueous solution was added to the reaction solution, and the mixture was then extracted with ethyl acetate. The resultant organic layer was washed with saturated brine, and then the solvent was distilled off under reduced pressure. The resultant residue was purified by column chromatography (silica gel:ethyl acetate/n-hexane=3:7) to obtain the object compound (166 mg, yield 52%).

Provenance & Evidence