Thiomorpholine → 2-[(1S)-6-(4-Thiomorpholinyl)-3,4-dihydro-1H-2-benzopyran-1-yl]ethanol

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Reaction Steps

2-((1S)-6-Bromo-3,4-dihydro-1H-2-benzopyran-1-yl)ethanol (0.26 g, 0.99 mmol) was dissolved in dry toluene (10 mL) and degassed. Thiomorpholine (0.14 mL, 1.48 mmol), tris(dibenzylideneacetone)dipalladium (51 mg), (+/−)-2,2′-bis(diphenylphosphino)-1,1′-binaphthyl (77 mg) and sodium tert-butoxide (0.126 g, 1.3 mmol) were added and the mixture heated under reflux with stirring, under a nitrogen atmosphere, for 24 h. The reaction was cooled to room temperature, diluted with dichloromethane, filtered through celite and washed with water. The organic extracts were dried (MgSO4), filtered and evaporated in vacuo. The crude product was purified by flash chromatography on silica, to yield the title compound.

Provenance & Evidence