Sodium Bicarbonate → HCID 69144950, compound

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Reaction Steps

To a suspension of 4-(p-toluidino)piperidine ditrifluoroacetate (synthesized in Preparation Example 4-5) (0.63 g) in 1,2-dichloroethane (3 mL) was added triethylamine (0.42 mL). The suspension was stirred at room temperature for 25 minutes. Then, to the suspension was added [1-benzyl-4-[2-(tert-butyldiphenylsiloxy)ethyl]piperidin-4-yl]acetaldehyde (synthesized in Example 85) (0.75 g) in 1,2-dichloroethane (1.5 mL), and it was stirred at room temperature for additional 5 minutes. The reaction solution was ice-cooled, to which sodium triacetoxyborohydride (0.50 g) was added. After allowing the temperature to rise to room temperature, the solution was stirred for additional 15 hours. Saturated aqueous sodium bicarbonate solution was and it was extracted with ethyl acetate. The organic layer was washed with saturated aqueous sodium chloride solution, dried over anhydrous magnesium sulfate and concentrated under reduced pressure. The resulting residue was purified by chromatography [NH silica gel, ethyl acetate-chloroform (5:95)] to give the title compound (0.87 g).

Provenance & Evidence