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

Participants

Reaction Steps

To a suspension of 4-(p-toluidino)piperidine trifluoroacetate (synthesized in Preparation Example 4-5) (656 mg) in tetrahydrofuran (5 mL) was added triethylamine (0.44 mL). The solution was stirred at room temperature for 25 minutes. Then, 3,9-dioxaspiro[5.5]undecan-2-ol (synthesized in Example 79) (135 mg) in tetrahydrofuran (3 mL) was added to the solution and it was stirred at room temperature for additional 5 minutes. The reaction solution was ice-cooled and sodium triacetoxyborohydride (333 mg) was added thereto. After allowing the reaction solution for its temperature rise to room temperature, it was stirred for additional 26 hours. To the reaction solution was added a 3N aqueous sodium hydroxide solution (10 mL) and it was extracted with ethyl acetate.

Provenance & Evidence