(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 → HCID 18624687, compound

HRID 1940264Notes

Reaction equation

HRID 1940264 reaction equation
C1(CC[C@H](OC2CCCCO2)/C=C/[C@@H:12]2[C@@H:19]3[C@@H:15]([O:16][C:17](=[O:20])[CH2:18]3)[CH2:14][C@H:13]2OC2CCCCO2)C=CC=CC=1>CCOC(C)=O.[Pd].[C]>[O:16]1[C:17](=[O:20])[CH:18]=[C:19]2[CH:12]=[CH:13][CH:14]=[C:15]12

Participants

4

Reactant 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-one

Product 1

HCID 18624687HCID 18624687, compoundYield 403.9%

Reagents, catalysts & solvents 2

HCID 178418390HCID 178418390, compoundCatalystHCID 8857Ethyl AcetateSolvent

Procedure

A solution of the lactone 6 (6.44 g, 13.4 mmol) in 50 mL of EtOAc was hydrogenated in the presence of 10% Pd/carbon (0.15 g) at 40 psi in a Parr hydrogenation apparatus for 4 h. The reaction mixture was filtered through Celite and the filtrate was concentrated to afford 7 (6.5 g, 99% yield) as a colorless oil. 1H-NMR (CDCl3) δ (characteristic peaks only) 7.22 (m, 5H), 5.00 (m, 1H), 4.76 (m, 2H), 3.52 (m, 2H).

Workup

  1. filtrationThe reaction mixture was filtered through Celite
  2. concentrationthe filtrate was concentrated

Sources & evidence

ORD record
ord-14b3302a5836459bbecb1533cbcdcc5a
Source dataset
uspto-grants-1997_12
Patent number
US05698733

Reaction notes

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