HCID 57672522, compound → HCID 57672404, compound

HRID 2101791Notes

Reaction equation

HRID 2101791 reaction equation
[CH3:1][C:2]1[CH:3]=[C:4]([C@H:16]([CH2:22][CH2:23][CH3:24])[CH2:17][C:18]([O:20][CH3:21])=[O:19])[CH:5]=[CH:6][C:7]=1[O:8]CC1C=CC=CC=1>[Pd].CCOC(C)=O>[OH:8][C:7]1[CH:6]=[CH:5][C:4]([C@H:16]([CH2:22][CH2:23][CH3:24])[CH2:17][C:18]([O:20][CH3:21])=[O:19])=[CH:3][C:2]=1[CH3:1]

Participants

4

Reactant 1

HCID 57672522HCID 57672522, compound

Product 1

HCID 57672404HCID 57672404, compoundYield 34%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 8857Ethyl AcetateSolvent

Procedure

To a flask containing 27.3 (0.4140 g, 1.268 mmol) under an atmosphere of nitrogen was added 10% Pd/C (0.20 g, 1.88 mmol). The flask was sealed with a rubber septum. To this system was added EtOAc (10 mL) and then vacuum was applied followed by addition of H2 gas (this was repeated three times). A balloon was placed on the flask and the reaction was stirred under H2 overnight. The reaction was filtered, concentrated, and purified by silica gel chromatography (0 to 20% EtOAc/hexanes) to afford a 27.4 (0.102 g, 34% yield).

Workup

  1. customThe flask was sealed with a rubber septum
  2. additionvacuum was applied followed by addition of H2 gas (
  3. filtrationThe reaction was filtered
  4. concentrationconcentrated
  5. custompurified by silica gel chromatography (0 to 20% EtOAc/hexanes)

Sources & evidence

ORD record
ord-21cded89bedc4d9a8d7cb9cb952e3f09
Source dataset
uspto-grants-2009_08
Patent number
US07572934B2

Reaction notes

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