Sodium Hydroxide → 2-Piperidinecarboxylic acid, 1-benzoyl-2-methyl-

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Reaction Conditions

Reaction Steps

Ethyl-1-benzoyl-2-methyl-piperidine-2-carboxylate (6.49 g, 23.51 mmol) was dissolved in EtOH (54 mL) and H2O (16 mL). NaOH (2.75 g, 68.6 mmol) was added and the reaction was heated to 40° C. for 1 h. An additional portion of NaOH (2.75 g, 68.6 mmol) was added and the reaction was heated to 65° C. for 1 h. The ethanol was removed and the residue was diluted with 50 mL of H2O. The pH was adjusted to ~2 with HCl (c). The aqueous layer was extracted 3× with ether and ethyl acetate. Removal of solvent provided 0.75 g, 22% yield of 1-benzoyl-2-methyl-piperidine-2-carboxylic acid. 1H NMR (200 MHz, DMSO) δ1.4 (s, 3H), 1.5-1.9 (comp m, 4H), 3.0 (m, 2H), 3.4 (m, 2H), 7.4 (m, 5H).

Provenance & Evidence