Sodium Hydroxide → 2-[1-[2-[4-(p-Toluidino)piperidin-1-yl]ethyl]cyclobutyl]ethanol

Participants

Reaction Steps

To a suspension of 4-(p-toluidino)piperidine trifluoroacetate (418 mg) (synthesized in Preparation Example 4-5) in tetrahydrofuran (3 mL) was added triethylamine (0.28 mL). The solution was stirred at room temperature for 5 minutes. Then, 7-oxaspiro[3.5]nonan-6-ol (104 mg) (synthesized in Example 65) in tetrahydrofuran (3 mL) was added to the solution and it was stirred at room temperature for additional 10 minutes. The reaction solution was ice-cooled and sodium triacetoxyborohydride (424 mg) was added thereto. The solution was then 4lowed for its temperature to rise to room temperature. The solution was stirred for additional 4.5 hours. A 3N aqueous sodium hydroxide solution (5 mL) was added to the reaction solution and it was extracted with tert-butyl methyl ether. The resulting residue was purified by chromatography [NH silica gel, hexane-ethyl acetate (7:3)] to give the title compound (175 mg).

Provenance & Evidence