Triethylamine → Methyl 3-[3-(tert-butoxycarbonylamino)piperidin-1-yl]benzoate

참여 물질

반응 단계

3-(tert-Butoxycarbonylamino)piperidine (200 mg, 1.00 mmol), 3-(methoxycarbonyl)phenylboric acid (360 mg, 2.00 mmol) and molecular sieves 4 Å (100 mg) were suspended in dichloromethane (10 mL). To this suspension, copper (II) acetate (182 mg, 1.00 mmol) and triethylamine (0.280 mL, 2.00 mmol) were added and the mixture was stirred at room temperature for 15 hours. Subsequently, the reaction mixture was filtered through Celite and a saturated aqueous sodium bicarbonate solution was added to the filtrate. This mixture was extracted with ethyl acetate and the extract washed with brine, followed by drying over magnesium sulfate and evaporation of the solvent. The resulting residue was purified by silica gel column chromatography (hexane:ethyl acetate=10:1->5:1) to give a colorless oil. This product was further purified by silica gel column chromatography (Chromatorex NH-DM2035 (Fuji Sylysia Chemical Co., Ltd.) hexane:ethyl acetate=10:1) to give 154 mg (46%) of the desired compound as a colorless powder.

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