HCID 70005765, compound → HCID 54404731, compound

HRID 1860527Notes

Reaction equation

HRID 1860527 reaction equation
[CH3:1][O:2][C:3](=[O:30])[CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][C@@H:10]1[C:14](=[O:15])[CH2:13][CH2:12][C@H:11]1[CH:16]=[CH:17][C:18]([C:20]1[C:29]2[C:24](=[CH:25][CH:26]=[CH:27][CH:28]=2)[CH:23]=[CH:22][CH:21]=1)=[O:19]>[Pd].C(OCC)(=O)C>[CH3:1][O:2][C:3](=[O:30])[CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][C@@H:10]1[C:14](=[O:15])[CH2:13][CH2:12][C@H:11]1[CH2:16][CH2:17][C:18]([C:20]1[C:29]2[C:24](=[CH:25][CH:26]=[CH:27][CH:28]=2)[CH:23]=[CH:22][CH:21]=1)=[O:19]

Participants

4

Reactant 1

HCID 70005765HCID 70005765, compound

Product 1

HCID 54404731HCID 54404731, compoundYield 69.5%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 8857Ethyl AcetateSolvent

Procedure

A mixture of trans-7-[2-(3-naphthalen-1-yl-3-oxo-propenyl)-5-oxo-cyclopentyl]-heptanoic acid methyl ester of Step A (143 mg, 0.352 mmol), 10% palladium on carbon (100 mg), and ethyl acetate (10 mL) were hydrogenated on a Parr shaker at 50 psi for 1.5 h. The catalyst was removed via filtration through Celite®. The filtrate was concentrated and the residue was purified by radial chromatography (hexanes to 25% ethyl acetate in hexanes) to provide the title compound of Step B (100 mg) as a clear and colorless oil. MS 426 (M+18).

Workup

  1. customThe catalyst was removed via filtration through Celite®
  2. concentrationThe filtrate was concentrated
  3. customthe residue was purified by radial chromatography (hexanes to 25% ethyl acetate in hexanes)

Sources & evidence

ORD record
ord-3265510745084877b188d7c4ba019bdb
Source dataset
uspto-grants-2003_03
Patent number
US06531485B2

Reaction notes

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