p-Toluenesulfonic acid monohydrate → (6Z,8aR,9R,10R,11aS)-4,5,8,8a,9,10,11, 11a-octahydro-10-hydroxy-9-((S,E)-3-hydroxy-5-phenylpent-1-enyl)cyclopenta[b]oxecin-2(3H)-one

HRID 517406Notes

Reaction equation

HRID 517406 reaction equation
O.C1(C)C=CC(S(O)(=O)=O)=CC=1.[C:13]1([CH2:19][CH2:20][C@H:21]([O:45]C2CCCCO2)/[CH:22]=[CH:23]/[C@@H:24]2[C@@H:36]3[C@@H:27]([O:28][C:29](=[O:37])[CH2:30][CH2:31][CH2:32][CH:33]=[CH:34][CH2:35]3)[CH2:26][C@H:25]2[O:38]C2CCCCO2)[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1>CO>[OH:38][C@@H:25]1[CH2:26][C@@H:27]2[O:28][C:29](=[O:37])[CH2:30][CH2:31][CH2:32][CH:33]=[CH:34][CH2:35][C@@H:36]2[C@H:24]1/[CH:23]=[CH:22]/[C@@H:21]([OH:45])[CH2:20][CH2:19][C:13]1[CH:14]=[CH:15][CH:16]=[CH:17][CH:18]=1

Participants

4

Reactant 2

HCID 521998p-Toluenesulfonic acid monohydrateHCID 117875096(6Z,8aR,9R,10R,11aS)-4,5,8,8a,9,10,11,11a-octahydro-9-((S,E)-5-phenyl-3-(tetra hydro-2H-pyran-2-yloxy)pent-1-enyl)-10-(tetrahydro-2H-pyran-2-yloxy)cyclopenta[b]oxecin-2(3H)-one

Product 1

HCID 49872499(6Z,8aR,9R,10R,11aS)-4,5,8,8a,9,10,11, 11a-octahydro-10-hydroxy-9-((S,E)-3-hydroxy-5-phenylpent-1-enyl)cyclopenta[b]oxecin-2(3H)-oneYield 56.6%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

p-Toluenesulfonic acid monohydrate (0.16 g, 0.84 mmol) was added to a stirred solution of (6Z,8aR,9R,10R,11aS)-4,5,8,8a,9,10,11,11a-octahydro-9-((S,E)-5-phenyl-3-(tetrahydro-2H-pyran-2-yloxy)pent-1-enyl)-10-(tetrahydro-2H-pyran-2-yloxy)cyclopenta[b]oxecin-2(3H)-one (9.0 g, 16.7 mmol) in methanol (90 mL). The mixture was stirred for 2 hr at room temperature (TLC monitoring). Then, the reaction mixture was washed with saturated aqueous solution of sodium bicarbonate (100 mL). The organic layer was separated and the water layer was extracted with ethyl acetate (100 mL). The combined organic layers were dried over magnesium sulfate, filtered and concentrated under reduced pressure to give 9.0 g of crude product. The crude product was purified by column chromatography providing 3.5 g of the title compound (56.5% yield).

Workup

  1. washThen, the reaction mixture was washed with saturated aqueous solution of sodium bicarbonate (100 mL)
  2. customThe organic layer was separated
  3. extractionthe water layer was extracted with ethyl acetate (100 mL)
  4. dry with materialThe combined organic layers were dried over magnesium sulfate
  5. filtrationfiltered
  6. concentrationconcentrated under reduced pressure
  7. customto give 9.0 g of crude product
  8. customThe crude product was purified by column chromatography

Sources & evidence

ORD record
ord-c7767e8da8734009acc161df27ca5b7e
Source dataset
uspto-grants-2015_08
Patent number
US09115109B2

Reaction notes

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