HCID 44206775, compound → HCID 57857068, compound

HRID 561756Notes

Reaction equation

HRID 561756 reaction equation
[S:1]1[C:5]([C@H:6]([OH:25])/[CH:7]=[CH:8]/[C@H:9]2[C@H:13]([OH:14])[CH2:12][C:11](=[O:15])[C@@H:10]2[CH2:16]/[CH:17]=[CH:18]\[CH2:19][CH2:20][CH2:21][C:22]([OH:24])=[O:23])=[CH:4][C:3]2[CH:26]=[CH:27][CH:28]=[CH:29][C:2]1=2.[H][H]>C(O)C.C1C=CC=CC=1.C1C=CC(P(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1.C1C=CC(P(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1.C1C=CC(P(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1.[Cl-].[Rh]>[S:1]1[C:5]([C@H:6]([OH:25])/[CH:7]=[CH:8]/[C@H:9]2[C@H:13]([OH:14])[CH2:12][C:11](=[O:15])[C@@H:10]2[CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][C:22]([OH:24])=[O:23])=[CH:4][C:3]2[CH:26]=[CH:27][CH:28]=[CH:29][C:2]1=2

Participants

6

Reactant 2

HCID 44206775HCID 44206775, compoundHCID 178418361HCID 178418361, compound

Product 1

HCID 57857068HCID 57857068, compound

Reagents, catalysts & solvents 3

HCID 84599Chlorotris(triphenylphosphine)rhodium(I)CatalystHCID 241BenzeneSolventHCID 702EthanolSolvent

Procedure

(Z)-7-((1R,2R,3R)-2-((R,E)-3-(Benzo[b]thiophen-2-yl)-3-hydroxyprop-1-enyl)-3-hydroxy-5-oxocyclopentyl)hept-5-enoic acid (Example 7, 1 molar equivalent) is dissolved in a 3:2 mixture of ethanol and benzene (0.01 M) under a nitrogen atmosphere. Wilkinson's catalyst (30% by weight relative to starting material) is added and hydrogen gas is introduced. The hydrogen uptake is monitored and upon theoretical consumption, the solvents are removed under reduced pressure and the residue is dissolved in a minimal amount of ethyl acetate containing 1% acetic acid. The crude product is purified using a filtration column on silica gel, eluted with 0.4% acetic acid in ethyl acetate. A second flash silica column eluted with an isopropanol-hexanes-acetic acid solvent system affords the title compound.

Workup

  1. customThe hydrogen uptake is monitored and upon theoretical consumption
  2. customthe solvents are removed under reduced pressure
  3. dissolutionthe residue is dissolved in a minimal amount of ethyl acetate containing 1% acetic acid
  4. customThe crude product is purified
  5. filtrationa filtration column on silica gel
  6. washeluted with 0.4% acetic acid in ethyl acetate
  7. washA second flash silica column eluted with an isopropanol-hexanes-acetic acid solvent system

Sources & evidence

ORD record
ord-89305d92183543c68f8c5c34edf126f9
Source dataset
uspto-grants-2011_11
Patent number
US08063240B2

Reaction notes

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