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

HRID 1272584Notes

Reaction equation

HRID 1272584 reaction equation
[CH2:1]([O:3][C:4](=[O:29])[CH2:5][C:6](=[O:28])/[CH:7]=[CH:8]/[C:9]1[N:10]([CH:25]([CH3:27])[CH3:26])[C:11]2[C:16]([C:17]=1[C:18]1[CH:23]=[CH:22][C:21]([F:24])=[CH:20][CH:19]=1)=[CH:15][CH:14]=[CH:13][CH:12]=2)[CH3:2].C(O)=O.CCN(CC)CC.C([O-])(O)=O.[Na+]>CN(C=O)C.CC(OC)(C)C.CCCCCC.CC(OC)(C)C>[CH2:1]([O:3][C:4](=[O:29])[CH2:5][C@H:6]([OH:28])/[CH:7]=[CH:8]/[C:9]1[N:10]([CH:25]([CH3:26])[CH3:27])[C:11]2[C:16]([C:17]=1[C:18]1[CH:23]=[CH:22][C:21]([F:24])=[CH:20][CH:19]=1)=[CH:15][CH:14]=[CH:13][CH:12]=2)[CH3:2]

Participants

8

Reactant 4

HCID 284Formic AcidHCID 8471TriethylamineHCID 516892Sodium BicarbonateHCID 20730393(E)-5-[3-(4-Fluorophenyl)-1-isopropyl-1H-indol-2-yl]-3-oxopent-4-enoic Acid Ethyl Ester

Product 1

HCID 11741405(E)-(S)-5-[3-(4-Fluoro-phenyl)-1-isopropyl-1H-indol-2-yl]-3-hydroxy-pent-4-enoic acid ethyl ester

Reagents, catalysts & solvents 3

HCID 6228DimethylformamideSolventHCID 15413tert-Butyl methyl etherSolventHCID 21982663Methyl t-butylether hexaneSolvent

Procedure

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

Workup

  1. extractionStandard aquous work-up with NaCl solution and extraction with MTBE and removel of the solvent
  2. customgive the crude product

Sources & evidence

ORD record
ord-f6bca80ac42f4670b184c7f027891b02
Source dataset
uspto-grants-2007_04
Patent number
US07208623B2

Reaction notes

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