Cesium carbonate → (1R,5S)-3-(3-nitrophenyl)-8-oxa-3-azabicyclo[3.2.1]octane

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Reaction Conditions

Reaction Steps

The mixture of 1-bromo-3-nitrobenzene (0.15 g, 0.743 mmol), (1R,5S)-8-oxa-3-azabicyclo[3.2.1]octane hydrochloride (0.122 g, 0.82 mmol), Pd2(dba)3 (0.043 g, 0.074 mmol), X-Phos (0.071 g, 0.15 mmol) and Cs2CO3 (0.727 g, 2.23 mmol) in dioxane (30 mL) was heated to 100° C. for 16 h under N2 atmosphere. Then it was concentrated to dryness. The residue was purified by column chromatography (silica gel, 200˜300 mesh, eluting with ethyl acetate:petroleum ether=1:8) to afford (1R,5S)-3-(3-nitrophenyl)-8-oxa-3-azabicyclo[3.2.1]octane (0.12 g, 69%) as a brown solid. LC-MS: 235 [M+H]+, tR=1.57 min.

Provenance & Evidence