Hydrochloric Acid → (3S,6R)-6-Methylpiperidine-3-carboxylic acid

Participants

Reaction Conditions

Reaction Steps

Into a 75 mL sealable tube, were added 3-methyl 1-(phenylmethyl) (3S,6R)-6-methyl-1,3-piperidinedicarboxylate (10 g, 34.3 mmol), 1,4-dioxane (20 mL) and concentrated HCl (20 mL), and the mixture was stirred at 100° C. for 3 hours. The mixture was then cooled to room temperature. HPLC showed no starting material and NMR showed major was the desired product. The solution was transfered to a 500 mL round bottom flask, and concentrated to dryness. Trituration with Et2O and CH3CN afforded the HCl salt of the title compound (6.17 g) as a colorless oil that turned into a white solid after standing overnight. 1H NMR (400 MHz, CD3OD): δ 6.51 (s, 1H), 7.04 (m, 1H), 7.32 (m, 2H), 7.46 (dd, J=8.6, 1.3 Hz, 1H), 7.66 (m, 2H), 7.75 (dd, J=8.3, 0.8 Hz, 1H), 7.81 (s, 1H).

Provenance & Evidence