Triphenylphosphine → (S)-8-Fluoro-5-(4-methoxy-benzenesulfonyl)-6-methyl-5,6-dihydrophenanthridine

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Reaction Steps

N-{4′-fluoro-2′-[(1R)-1-hydroxyethyl]-1,1′-biphenyl-2-yl}-4-methoxybenzene-sulfonamide (0.12 g, 0.29 mmol) and triphenylphosphine (0.31 g, 1.2 mmol) were dissolved in tetrahydrofuran (10 mL) and diethylazodicarboxylate (0.21 g, 0.19 mL, 1.2 mmol) was added. The solution was stirred overnight at room temperature. The solution was concentrated in vacuo and the mixture was dissolved in ethyl acetate and washed with water. The organic phase was dried over anhydrous magnesium sulfate, filtered, and concentrated in vacuo. The crude product was purified by flash chromatography on silica gel (3:1 hexane: ethyl acetate) to yield the title compound as a crystalline solid (0.085 g, 79% ), m.p. 181-182° C.

Provenance & Evidence