3,4-dihydro-2H-pyran → HCID 11102783, compound

HRID 517385Notes

Reaction equation

HRID 517385 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[CH2:11][CH2:12][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+]>C1COCC1.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)[CH2:12][CH2:11][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 10267038(3aR,4R,5R,6aS)-5-Hydroxy-4-[(3R)-3-hydroxy-5-phenylpentyl]hexahydro-2H-cyclopenta[b]furan-2-one

Product 1

HCID 11102783HCID 11102783, compoundYield 95%

Reagents, catalysts & solvents 2

HCID 521998p-Toluenesulfonic acid monohydrateCatalystHCID 8028TetrahydrofuranSolvent

Procedure

p-Toluenesulfonic acid monohydrate (0.46 g, 2.4 mmol) was added to a solution of (3aR,4R,5R,6aS)-hexahydro-5-hydroxy-4-((R)-3-hydroxy-5-phenylpentyl)cyclopenta[b]furan-2-one (15.0 g, 49.3 mmol) and 3,4-dihydro-2H-pyran (12.4 g, 147.4 mmol) in THF (200 mL) at room temperature and the mixture was stirred for 2.5 hr (TLC monitoring). Saturated aqueous solution of sodium bicarbonate (200 mL) was poured into reaction mixture and the reaction was stirred for 5 minutes. The organic layer was separated and the aqueous layer was extracted with ethyl acetate (200 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 26.0 g of crude product. The crude product was purified by column chromatography and then concentrated under reduced pressure to provide 22.1 g of the title compound (95.0% yield).

Workup

  1. stirringthe reaction was stirred for 5 minutes
  2. customThe organic layer was separated
  3. extractionthe aqueous layer was extracted with ethyl acetate (200 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 26.0 g of crude product
  8. customThe crude product was purified by column chromatography
  9. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-de7a5edb3d314945bbc295c035b063b1
Source dataset
uspto-grants-2015_08
Patent number
US09115109B2

Reaction notes

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