Formic Acid → (E)-(S)-5-[3-(4-Fluoro-phenyl)-1-isopropyl-1H-indol-2-yl]-3-hydroxy-pent-4-enoic acid ethyl ester

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Reaction Steps

A solution of (E)-5-[3-(4-Fluoro-phenyl)-1-isopropyl-1H-indol-2-yl]-3-oxo-pent-4-enoic acid ethyl ester (2.0 g, 5.08 mmol), Ru[(1R,2R)-p-TsNCH(C6H5)CH(C6H5)NH2]Cl(η6-p-cymene) (12.8 mg, 0.025 mmol) and a mixture of HCOOH (1.40 g, 30.5 mmol)/NEt3 (1.23 g, 12.2 mmol) is heated in DMF (8.0 ml) at 50° C. for 21 h. After that the solution is diluted with MTBE (5 ml) and neutralised with NaHCO3 (4 ml). Standard aquous work-up with NaCl solution and extraction with MTBE and removel of the solvent give the crude product. Chromatography on silica gel using a 4:1 hexane-MTBE mixture as eluent to afford of (E)-(S)-5-[3-(4-Fluoro-phenyl)-1-isopropyl-1H-indol-2-yl]-3-hydroxy-pent-4-enoic acid ethyl ester. MS: 395.48

Provenance & Evidence