Hydrochloric Acid → HCID 66794539, compound

Participants

Reaction Steps

To a solution of methyl 12-cyclohexyl-4-{N-[2-oxo-2-(piperidin-1-yl)ethyl]-N-propylamino}-6,7-dihydro-5-oxa-7a-azadibenzo[a,e]azulene-9-carboxylate (3.63 g, 6.51 mmol) in tetrahydrofuran (7 ml) was added a solution (50 ml) of 1M BH3 THF complex in tetrahydrofuran under ice-cooling, and the mixture was stirred at room temperature for 11 hr. 4N Hydrochloric acid was added to the reaction mixture under ice-cooling, and the mixture was stirred at 65° C. for 3 hr. The reaction mixture was adjusted to pH 8 with 4N aqueous sodium hydroxide solution, and extracted with ethyl acetate. The organic layer was washed with saturated brine and dried over anhydrous sodium sulfate. After filtration, the solvent was evaporated under reduced pressure, and the residue was purified by silica gel column chromatography (chloroform:methanol=35:1-15:1) to give methyl 12-cyclohexyl-4-{N-[2-(piperidin-1-yl)ethyl]-N-propylamino}-6,7-dihydro-5-oxa-7a-azadibenzo[a,e]azulene-9-carboxylate (3.25 g, yield 92%).

Provenance & Evidence