HCID 57672454, compound → HCID 57672483, compound

HRID 2101804Notes

Reaction equation

HRID 2101804 reaction equation
[OH:1][C:2]1[CH:7]=[CH:6][C:5]([C@@H:8]([C:14]#[C:15][CH2:16][CH3:17])[CH2:9][C:10]([O:12][CH3:13])=[O:11])=[CH:4][CH:3]=1>CCOC(C)=O.[Pd]>[OH:1][C:2]1[CH:3]=[CH:4][C:5]([C@H:8]([CH2:14][CH2:15][CH2:16][CH3:17])[CH2:9][C:10]([O:12][CH3:13])=[O:11])=[CH:6][CH:7]=1

Participants

4

Reactant 1

HCID 57672454HCID 57672454, compound

Product 1

HCID 57672483HCID 57672483, compoundYield 95%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 8857Ethyl AcetateSolvent

Procedure

To a stirred solution of 25.1 (0.067 g, 0.3 mmol) in EtOAc (3 mL) at 23° C. was added palladium on carbon (0.03 g, 0.3 mmol). The reaction was placed under an atmosphere of hydrogen and then stirred at room temperature. After 5 hours, the reaction mixture was filtered through a pad of silica gel and then concentrated. After concentration, the residue was purified on silica gel (0%-20% EtOAc/hexane) to give 37.1 (0.065 g, 95%). MS ESI (pos.) m/e: 237.1 (M+H)+.

Workup

  1. filtrationthe reaction mixture was filtered through a pad of silica gel
  2. concentrationconcentrated
  3. concentrationAfter concentration
  4. customthe residue was purified on silica gel (0%-20% EtOAc/hexane)

Sources & evidence

ORD record
ord-537801d75ca84e7faa36f59846c0e386
Source dataset
uspto-grants-2009_08
Patent number
US07572934B2

Reaction notes

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