Cesium carbonate → (6R,7S)-7-dibenzylamino-6-ethyl-2-fluoro-9-(2,2,2-trifluoro-ethyl)-6,7-dihydro-9H-5-oxa-9-aza-benzocyclohepten-8-one

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Reaction Steps

A solution of 0.50 g (1.24 mmol) (−)-(6R,7S)-7-dibenzylamino-6-ethyl-2-fluoro-6,7-dihydro-9H-5-oxa-9-aza-benzocyclohepten-8-one and 0.44 g (1.85 mmol) 2,2,2-trifluoroethyl triflate in 5 ml dimethylformamide were treated with 0.61 g (1.85 mmol) cesium carbonate for 18 hours. The mixture was extracted with water/ethylacetate. Chromatography on silicagel with heptane/ethylacetate 70:30 yielded 0.34 g (57%) (6R,7S)-7-dibenzylamino-6-ethyl-2-fluoro-9-(2,2,2-trifluoro-ethyl)-6,7-dihydro-9H-5-oxa-9-aza-benzocyclohepten-8-one, MS m/e (%): 487.4 (M+H+, 100).

Provenance & Evidence