Acetic Acid → (3aR,4R,5R,6aS)-5-Hydroxy-4-((3R,4R,E)-3-hydroxy-4-(m-tolyl)pent-1-en-1-yl)hexahydro-2H-cyclopenta[b]furan-2-one

HRID 331532Notes

Reaction equation

HRID 331532 reaction equation
[OH:1][C@@H:2]([C@@H:23]([C:25]1[CH:26]=[C:27]([CH3:31])[CH:28]=[CH:29][CH:30]=1)[CH3:24])/[CH:3]=[CH:4]/[C@H:5]1[C@H:12]([O:13]C(=O)C2C=CC=CC=2)[CH2:11][C@H:10]2[C@@H:6]1[CH2:7][C:8](=[O:22])[O:9]2.C(=O)([O-])[O-].[K+].[K+].C(O)(=O)C>CO>[OH:1][C@@H:2]([C@@H:23]([C:25]1[CH:26]=[C:27]([CH3:31])[CH:28]=[CH:29][CH:30]=1)[CH3:24])/[CH:3]=[CH:4]/[C@H:5]1[C@H:12]([OH:13])[CH2:11][C@H:10]2[C@@H:6]1[CH2:7][C:8](=[O:22])[O:9]2

Participants

5

Reactant 3

HCID 176Acetic AcidHCID 11430Potassium CarbonateHCID 67108705(1S,5R,6R,7R)-6-[(1E,3R,4R)-3-hydroxy-4-(m-tolyl)-1-pentenyl]-7-benzoyloxy-2-oxabicyclo[3.3.0]octan-3-one

Product 1

HCID 67108750(3aR,4R,5R,6aS)-5-Hydroxy-4-((3R,4R,E)-3-hydroxy-4-(m-tolyl)pent-1-en-1-yl)hexahydro-2H-cyclopenta[b]furan-2-one

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent2×

Procedure

The crude alcohol, {(1S,5R,6R,7R)-6-[(1E,3R,4R)-3-hydroxy-4-(m-tolyl)-1-pentenyl]-7-benzoyloxy-2-oxabicyclo[3.3.0]octan-3-one} (649.9 g) synthesized in Example 4 was dissolved in methanol (740 mL), potassium carbonate (116.3 g) was added, and the mixture was stirred at room temperature for 17 hr. Acetic acid was added to adjust to pH 7, methanol was evaporated, water was added, and the mixture was extracted with ethyl acetate. The extract was purified by silica gel column chromatography (hexane/ethyl acetate=4/1-0/1) to give the title compound (22.3 g). The structural property was as described below.

Workup

  1. customwas evaporated
  2. additionwater was added
  3. extractionthe mixture was extracted with ethyl acetate
  4. customThe extract was purified by silica gel column chromatography (hexane/ethyl acetate=4/1-0/1)

Sources & evidence

ORD record
ord-051878ed15094efe9185dfdce96aae2a
Source dataset
uspto-grants-2014_11
Patent number
US08877787B2

Reaction notes

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