Br[C:2]1[CH:3]=[CH:4][C:5]2[C@H:10]([CH2:11][CH2:12][OH:13])[O:9][CH2:8][CH2:7][C:6]=2[CH:14]=1.[O:15]1[CH2:19][CH2:18][NH:17][C:16]1=[O:20].[C@@H]1(N)CCCC[C@H]1N.C(=O)([O-])[O-].[K+].[K+].N>O1CCOCC1.[Cu]I>[OH:13][CH2:12][CH2:11][C@H:10]1[C:5]2[CH:4]=[CH:3][C:2]([N:17]3[CH2:18][CH2:19][O:15][C:16]3=[O:20])=[CH:14][C:6]=2[CH2:7][CH2:8][O:9]1To a stirred solution of 2-((1S)-6-bromo-3,4-dihydro-1H-2-benzopyran-1-yl)ethanol (0.815 g, 3.17 mmol) in dry dioxan (5 mL) was added 1,3-oxazolidin-2-one (0.26 g, 2.95 mmol), trans-1,2-cyclohexanediamine (0.05 mL, 0.42 mmol), copper(I) iodide (0.040 g, 0.21 mmol) and potassium carbonate (1.02 g, 7.36 mmol), and the mixture heated at reflux under nitrogen overnight. 2M Ammonia was added and the mixture extracted into dichloromethane. The combined 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.
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