HCID 59541900, compound → HCID 59541955, compound

HRID 1893227Notes

Reaction equation

HRID 1893227 reaction equation
[O:1]=[C:2]1[CH2:7][CH2:6][C:5]([C:8]2[CH:9]=[CH:10][C:11]3[O:15][C:14](=[O:16])[NH:13][C:12]=3[CH:17]=2)=[CH:4][CH2:3]1>CO.[Pd]>[O:1]=[C:2]1[CH2:7][CH2:6][CH:5]([C:8]2[CH:9]=[CH:10][C:11]3[O:15][C:14](=[O:16])[NH:13][C:12]=3[CH:17]=2)[CH2:4][CH2:3]1

Participants

4

Reactant 1

HCID 59541900HCID 59541900, compound

Product 1

HCID 59541955HCID 59541955, compound

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

To a Parr hydrogenation flask was added a solution of 5-(4-oxo-cyclohex-1-enyl)-3H-benzooxazol-2-one (as prepared in the previous step, 180 mg, 0.79 mmol) in MeOH (10 mL) followed by 5% Pd/C (Aldrich, ˜100 mg). The reaction was charged with 40 psi H2 gas for 10 hours at room temperature. The catalyst was removed by passing the reaction solution through a pad of Celite. MeOH was added to washed the Celite column three times. The combined organic layers were concentrated in vacuo to give the title compound as a white solid.

Workup

  1. additionThe reaction was charged with 40 psi H2 gas for 10 hours at room temperature
  2. customThe catalyst was removed
  3. additionMeOH was added
  4. washto washed the Celite column three times
  5. concentrationThe combined organic layers were concentrated in vacuo

Sources & evidence

ORD record
ord-492221b3cfa64e0c82dbd77ba418a25c
Source dataset
uspto-grants-2013_08
Patent number
US08513229B2

Reaction notes

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