3,4-dihydro-2H-pyran → (3aR, 4R, 5R, 6aS) Hexahydro-4-[(E)-(3S)-5-phenyl-3-(tetrahydropyran-2-yloxy)-1-pentenyl]-5-(tetrahydropyran-2-yloxy)-2H-cyclopenta[b]furan-2-one

HRID 517401Notes

Reaction equation

HRID 517401 reaction equation
[OH:1][C@@H:2]1[CH2:10][C@@H:5]2[O:6][C:7](=[O:9])[CH2:8][C@@H:4]2[C@H:3]1/[CH:11]=[CH:12]/[C@@H:13]([OH:22])[CH2:14][CH2:15][C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1.[O:23]1[CH:28]=[CH:27][CH2:26][CH2:25][CH2:24]1.[C:29](=[O:32])(O)[O-].[Na+]>ClCCl.O.C1(C)C=CC(S(O)(=O)=O)=CC=1>[C:16]1([CH2:15][CH2:14][C@H:13]([O:22][CH:4]2[CH2:3][CH2:2][CH2:10][CH2:29][O:32]2)/[CH:12]=[CH:11]/[C@@H:3]2[C@@H:4]3[C@@H:5]([O:6][C:7](=[O:9])[CH2:8]3)[CH2:10][C@H:2]2[O:1][CH:28]2[CH2:27][CH2:26][CH2:25][CH2:24][O:23]2)[CH:17]=[CH:18][CH:19]=[CH:20][CH:21]=1

Participants

6

Reactant 3

HCID 80803,4-dihydro-2H-pyranHCID 516892Sodium BicarbonateHCID 1304641741639-74-1

Product 1

HCID 11102745(3aR, 4R, 5R, 6aS) Hexahydro-4-[(E)-(3S)-5-phenyl-3-(tetrahydropyran-2-yloxy)-1-pentenyl]-5-(tetrahydropyran-2-yloxy)-2H-cyclopenta[b]furan-2-oneYield 89.9%

Reagents, catalysts & solvents 2

HCID 521998p-Toluenesulfonic acid monohydrateCatalystHCID 6344DichloromethaneSolvent

Procedure

p-Toluenesulfonic acid monohydrate (0.3 g, 0.165 mmol) was added to a solution of (3aR,4R,5R,6aS)-hexahydro-5-hydroxy-4-((S,E)-3-hydroxy-5-phenylpent-1-enyl)cyclopenta[b]furan-2-one (10.0 g, 33.1 mmol) and 3,4-dihydro-2H-pyran (4.2 g, 49.7 mmol) in dichloromethane (100 mL) at room temperature and the mixture was stirred for 2.5 hr (TLC monitoring). Saturated aqueous solution of sodium bicarbonate (100 mL) was poured into the reaction mixture and the mixture was stirred for 5 minutes. The organic layer was separated and the aqueous layer was extracted with ethyl acetate (100 mL). The combined organic layers were dried over magnesium sulfate, the solid was filtered off and the filtrate was concentrated under reduced pressure to give 16.0 g of crude product. The crude product was purified by column chromatography and then concentrated under reduced pressure to provide 14.0 g of the title compound (89.9% yield).

Workup

  1. stirringthe mixture was stirred for 5 minutes
  2. customThe organic layer was separated
  3. extractionthe aqueous layer was extracted with ethyl acetate (100 mL)
  4. dry with materialThe combined organic layers were dried over magnesium sulfate
  5. filtrationthe solid was filtered off
  6. concentrationthe filtrate was concentrated under reduced pressure
  7. customto give 16.0 g of crude product
  8. customThe crude product was purified by column chromatography
  9. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-09ac1a3581ec4afab06de3b6d779e0fe
Source dataset
uspto-grants-2015_08
Patent number
US09115109B2

Reaction notes

Loading…