Ammonium Chloride → HCID 21699661, compound

Participants

Reaction Steps

Methyl 2-t-butoxycarbonyl-1,2,3,4-tetrahydro-benzo[b][1,6]-naphthyridine-10-carboxylate (1.14 g, 3.05 mmol) was dissolved in ethanol (3 ml), followed by adding thereto sodium tetrahydroborate (138.4 mg, 3.66 mmol) and then a solution of calcium chloride (338.5 mg, 3.05 mmol) in ethanol (3 ml) under ice-cooling, and the resulting mixture was stirred at room temperature for 4 hours and then at 60° C. for 3 hours. A saturated aqueous ammonium chloride solution was added to the reaction mixture, followed by extraction with ethyl acetate. The organic layer was washed with a saturated aqueous sodium chloride solution, dried over anhydrous sodium sulfate and then concentrated under reduced pressure, and the resulting residue was purified by a silica gel column chromatography (hexane/ethyl acetate=1/1) to obtain the desired compound (442 mg, 46%) as a yellow oil.

Provenance & Evidence