Hydrochloric Acid → 3-((1R,5S)-8-oxa-3-azabicyclo[3.2.1]octan-3-yl)aniline

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Reaction Steps

To a stirred solution of (1R,5S)-3-(3-nitrophenyl)-8-oxa-3-azabicyclo[3.2.1]octane (0.08 g, 0.341 mmol) and Zn (0.223 g, 3.41 mmol) in dioxane (10 mL) and H2O (2 mL) was added dropwise conc. HCl (0.34 mL, 3.41 mmol) at 25° C. for 2 h. It was adjusted to pH=8 by the addition of solid NaHCO3. It was filtered and the filtration was extracted with ethyl acetate (2×10 mL) and the extraction was concentrated to dryness. The residue was purified by column chromatography (silica gel, 200˜300 mesh, eluting with ethyl acetate:petroleum ether=1:2) to afford 3-((1R,5S)-8-oxa-3-azabicyclo[3.2.1]octan-3-yl)aniline (0.061 g, 88%) as a yellow oil. LC-MS: 205 [M+H]+, tR=1.09 min.

Provenance & Evidence