Trifluoroacetic acid → (2R)-N-Octyl-2-piperidinecarboxamide

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Reaction Steps

(R)-(+)-1-(tert-Butoxycarbonyl)-2-piperidinecarboxylic acid n-octyl amide (8) (1.00 g; 2.94 mmol) is dissolved in methylene chloride (40 mL) at ambient temperature. Trifluoroacetic acid (20 mL) is added and the solution is stirred for 7 hours at ambient temperature. The solution is concentrated in vacuo at 40° C. The residue is dissolved in methylene chloride (200 mL) and poured onto saturated sodium bicarbonate solution. The pH is adjusted to 9 with saturated potassium carbonate solution. The mixture is shaken and the layers separated. The water layer is extracted with methylene chloride (3 times, 50 mL each). The combined organic extracts are washed with water, dried over MgSO4, filtered, and concentrated in vacuo affording the desired product (23) as a solid. ISMS: MH+ 240.8

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