Lithium hydroxide, monohydrate → 1-Benzyl-5-(4-chloro-phenyl)-1,2,3,6-tetrahydro-pyridine-4-carboxylic acid

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Reaction Steps

A mixture of 0.555 g (1.26 mmol) 1-benzyl-5-(4-chloro-phenyl)-1,2,3,6-tetrahydro-pyridine-4-carboxylic acid ethyl ester and 261 mg (6.2 mmol) LiOH.H2O in 15 mL THF and 5 mL water was stirred at room temperature over night. The mixture was evaporated to dryness, taken up in ethyl acetate, acidified with HCl to pH=1 and extracted with ethyl acetate. The combined organic layers were washed with water, evaporated to dryness and the residue was subjected to preparative HPLC chromatography on reversed phase eluting with a gradient formed from acetonitrile, water and formic acid to yield after evaporation of the product containing fractions 0.254 g (50%) of the title compound as white solid. MS (m/e): 328.2 [(M+H)+].

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