Ethyl Acetate → 3-(4-Trifluoromethoxyphenyl)-3,9-diaza-bicyclo[3.3.1]nonane-2,4-dione

HRID 605565Notes

Reaction equation

HRID 605565 reaction equation
C([N:8]1[CH:13]2[CH2:14][CH2:15][CH2:16][CH:9]1[C:10](=[O:29])[N:11]([C:18]1[CH:23]=[CH:22][C:21]([O:24][C:25]([F:28])([F:27])[F:26])=[CH:20][CH:19]=1)[C:12]2=[O:17])C1C=CC=CC=1.C(OCC)(=O)C>[Pd].C(O)C>[F:28][C:25]([F:26])([F:27])[O:24][C:21]1[CH:22]=[CH:23][C:18]([N:11]2[C:12](=[O:17])[CH:13]3[NH:8][CH:9]([CH2:16][CH2:15][CH2:14]3)[C:10]2=[O:29])=[CH:19][CH:20]=1

Participants

5

Reactant 2

HCID 8857Ethyl AcetateHCID 670460419-Benzyl-3-(4-trifluoromethoxy-phenyl)-3,9-diaza-bicyclo[3.3.1]nonane-2,4-dione

Product 1

HCID 670459993-(4-Trifluoromethoxyphenyl)-3,9-diaza-bicyclo[3.3.1]nonane-2,4-dione

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent2×

Procedure

A mixture of 9-benzyl-3-(4-trifluoromethoxy-phenyl)-3,9-diaza-bicyclo[3.3.1]nonane-2,4-dione (120 mg, 0.3 mmol), 10% Pd/C (20 mg, 0.02 mmol Pd), ethyl acetate (8 mL), and ethanol (2 mL) were stirred vigorously under an atmosphere of H2. After 2 h, more ethanol (2 mL) was added. After an additional 16 h, the reaction was filtered through Celite and concentrated to give 3-(4-trifluoromethoxy-phenyl)-3,9-diaza-bicyclo[3.3.1]nonane-2,4-dione: MS (ESI): 315.4 (M+H).

Workup

  1. waitAfter an additional 16 h
  2. filtrationthe reaction was filtered through Celite
  3. concentrationconcentrated

Sources & evidence

ORD record
ord-0caf3b2582a34f4c8694732358ff1cf5
Source dataset
uspto-grants-2011_03
Patent number
US07915253B2

Reaction notes

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