Hydrochloric Acid → 1-[(Tert-butoxy)carbonyl]-4-ethylpiperidine-4-carboxylic acid

Participants

Reaction Steps

To a stirred solution of 1-tert-butyl 4-ethyl 4-ethylpiperidine-1,4-dicarboxylate (Intermediate 21-step 2, 10.0 g, 63.69. mmol) in 50 ml ethanol was added potassium hydroxide (8.0 g, 95.5 mmol) and the contents were refluxed for 16 hours. Upon completion of the reaction (monitored by TLC), the reaction mixture was diluted with water, acidified with 5% HCl and extracted with DCM. The organic layer was dried over Na2SO4 and concentrated under reduced pressure to furnish the title compound (8.2 g) as a light yellow liquid. 1H NMR (300 MHz, CDCl3): 1.44 (s, 9H); 2.07-2.11 (m, 2H); 2.28 (s, 1H); 2.82 (s, 2H); 2.92-2.95 (m, 1H); 3.46-3.52 (m, 3H); ES Mass: 280 (100%), [M+Na].

Provenance & Evidence