(+/-)-6-(3-Methoxy-phenyl)-7-oxa-3-aza-bicyclo[4.1.0]heptane-3-carboxylic acid tert-butyl ester → HCID 45074241, compound

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Reaction Steps

To a solution of (±)-6-(3-methoxy-phenyl)-7-oxa-3-aza-bicyclo[4.1.0]heptane-3-carboxylic acid tert-butyl ester (2 g) in methanol (115 mL) was added palladium on carbon 10% (10:90, palladium:carbon black, 400 mg). The mixture was shaken in a Parr apparatus under an atmosphere of hydrogen (50 PSI) overnight. Filtration through Celite and evaporation of the solvent provided the crude product. The product was purified by flash chromatography (Silicagel, EtOAc/hexanes) to give (±)-3-hydroxy-4-(3-methoxy-phenyl)-piperidine-1-carboxylic acid tert-butyl ester (1.79 g, 89% yield). 1H NMR (CDCl3): δ ppm 7.26 (s, 1H), 6.72-6.92 (m, 3H), 4.31 (br. s., 2H), 3.96 (br. s., 1H), 3.81 (s, 3H), 3.01 (d, J=13.4 Hz, 1H), 2.70-2.92 (m, 2H), 2.13-2.34 (m, 1H), 1.64 (br. s., 2H), 1.49 (s, 9H).

Provenance & Evidence