(+/-)-3-Fluoro-4-(3-methoxy-4-nitro-phenyl)-piperidine-1-carboxylic acid tert-butyl ester → (+/-)-4-(4-Amino-3-methoxy-phenyl)-3-fluoro-piperidine-1-carboxylic acid tert-butyl ester

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To a solution of (±)-3-fluoro-4-(3-methoxy-4-nitro-phenyl)-piperidine-1-carboxylic acid tert-butyl ester in methanol (10 mL) was added palladium on carbon 10% (1:9 palladium:carbon black, 40 mg). The mixture was shaken in a Parr apparatus under an atmosphere of hydrogen (35 PSI) overnight. Filtration through Celite and evaporation of the solvent provided crude (±)-4-(4-amino-3-methoxy-phenyl)-3-fluoro-piperidine-1-carboxylic acid tert-butyl ester (180 mg, 98%), which was used without purification. 1H NMR (CDCl3): δ ppm 6.63-6.71 (m, 3H), 4.52 (br. s., 2H), 4.05-4.26 (m, 1H), 3.85 (s, 3H), 3.74 (br. s., 2H), 2.63-2.86 (m, 3H), 1.88 (d, J=13.4 Hz, 1H), 1.62-1.79 (m, 1H), 1.49 (s, 9H).

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