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

(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

1. concentrationThe solution is concentrated in vacuo at 40° C
2. dissolutionThe residue is dissolved in methylene chloride (200 mL)
3. additionpoured onto saturated sodium bicarbonate solution
4. stirringThe mixture is shaken
5. customthe layers separated
6. extractionThe water layer is extracted with methylene chloride (3 times, 50 mL each)
7. washThe combined organic extracts are washed with water
8. dry with materialdried over MgSO4
9. filtrationfiltered
10. concentrationconcentrated in vacuo

ORD record

ord-fff79697c30e47578050f8513277664b

Source dataset

uspto-grants-2006_03

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US07018642B2