Hydrochloric Acid → 2,2-Dimethyl-propionic acid (3RS,4RS)-3-methyl-piperidin-4-yl ester

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Reaction Steps

Palladium hydroxide (20% on carbon, 1.5 g) is placed in a round-bottom flask under an argon atmosphere and covered with methanol, A solution of 2,2-dimethyl-propionic acid (3RS,4RS)-1-benzyl-3-methyl-piperidin-4-yl ester (4) (15 g, 51.8 mmol) in 300 ml of methanol is added, followed by an 1.3M methanolic HCl solution (62 ml, 78 mmol). Then the mixture is hydrogenated under normal pressure for 20 h. The solution is filtrated through celite and evaporated under reduced pressure. The residue is dissolved in diethyl ether and washed with 1N aqueous sodium hydroxide solution and brine. The combined organic layers are dried over Na2SO4 and evaporated under reduced pressure.

Provenance & Evidence