HCID 44206775, compound → HCID 57857066, compound

HRID 561757Notes

Reaction equation

HRID 561757 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(OCC)(=O)C.[Pd]>[S:1]1[C:5]([C@H:6]([OH:25])[CH2:7][CH2:8][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

5

Reactant 2

HCID 44206775HCID 44206775, compoundHCID 178418361HCID 178418361, compound

Product 1

HCID 57857066HCID 57857066, compound

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 8857Ethyl AcetateSolvent

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 ethyl acetate (0.05 M) under a nitrogen atmosphere. 10% Pd/C (10 mol %) is added and hydrogen gas is introduced. After stirring for several hours at room temperature the reaction mixture is filtered over Celite. The crude product is purified by flash chromatography on regular silica gel eluted with ethyl acetate-hexanes (+0.4% acetic acid) to afford the title compound.

Workup

  1. filtrationis filtered over Celite
  2. customThe crude product is purified by flash chromatography on regular silica gel
  3. washeluted with ethyl acetate-hexanes (+0.4% acetic acid)

Sources & evidence

ORD record
ord-73e34a22236748979a9ae26fa0fdebbd
Source dataset
uspto-grants-2011_11
Patent number
US08063240B2

Reaction notes

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