4-(7-fluoro-3-methoxycarbonylmethyl-naphthalen-1-yl)-3,6-dihydro-2H-pyridine-1-carboxylic acid tert-butyl ester → 4-(7-Fluoro-3-methoxycarbonylmethyl-naphthalen-1-yl)-piperidine-1-carboxylic acid tert-butyl ester

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Reaction Steps

10% Palladium on carbon (0.09 g) was added to a deoxygenated solution of 4-(7-fluoro-3-methoxycarbonylmethyl-naphthalen-1-yl)-3,6-dihydro-2H-pyridine-1-carboxylic acid tert-butyl ester (which may be prepared as described above; 0.64 g, 1.6 mmol) in ethanol (30 mL) in a Parr shaker vessel. The mixture was hydrogenated at 60 psi for 16 h and then filtered through a pad of celite. The celite was washed with ethanol (2×5 mL) and the combined filtrates were concentrated under reduced pressure. The residue was purified by silica gel column chromatography (100-200 mesh), using 20% ethyl acetate/hexanes as eluent, to give 4-(7-fluoro-3-methoxycarbonylmethyl-naphthalen-1-yl)-piperidine-1-carboxylic acid tert-butyl ester (0.40 g, 62%) as a sticky colorless solid. MS cald. for C23H29FNO4 [(M+H)+] 402, obsd. 402.4.

Provenance & Evidence