Sodium Bicarbonate → Tert-butyl {1-[(2-oxo-1,2,3,4-tetrahydroquinolin-7-yl)methyl]piperidin-4-yl}carbamate

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Reaction Steps

A solution of the compound (19.8 g) obtained in Step 1-4 and tert-butyl piperidin-4-ylcarbamate (24.8 g) in CHCl3 (450 mL) was stirred at 70° C. for 1.5 hours and allowed to cool to room temperature. Thereafter, NaBH(OAc)3 (35.9 g) was added to the mixture under ice cooling and the mixture was stirred at room temperature for 12 hours. A saturated aqueous NaHCO3 solution was added to the reaction mixture and then a water layer and an organic layer were separated. The water layer was extracted three times with CHCl3. The combined organic layers were dried over Na2SO4 and concentrated under reduced pressure. The residue was purified by column chromatography (silica gel 60 N, mobile phase: MeOH/CHCl3=33/66 to 100/0; v/v) to obtain tert-butyl {1-[(2-oxo-1,2,3,4-tetrahydroquinolin-7-yl)methyl]piperidin-4-yl}carbamate (37.8 g, a colorless solid).

Provenance & Evidence