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

HRID 2110156Notes

Reaction equation

HRID 2110156 reaction equation
CC(=O)CC(=O)CCCCC.C([N:19]1[CH:24]2[CH2:25][CH2:26][CH2:27][CH:20]1[C:21](=[O:40])[N:22]([C:29]1[CH:34]=[CH:33][C:32]([O:35][C:36]([F:39])([F:38])[F:37])=[CH:31][CH:30]=1)[C:23]2=[O:28])C1C=CC=CC=1.C(OCC)(=O)C>[Pd].C(O)C>[F:39][C:36]([F:37])([F:38])[O:35][C:32]1[CH:33]=[CH:34][C:29]([N:22]2[C:23](=[O:28])[CH:24]3[NH:19][CH:20]([CH2:27][CH2:26][CH2:25]3)[C:21]2=[O:40])=[CH:30][CH:31]=1

Participants

6

Reactant 3

HCID 8857Ethyl AcetateHCID 803142,4-NonanedioneHCID 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

3-(4-trifluoromethoxy-phenyl)-3,9-diaza-bicyclo|3.3.1|nonane-2,4-dione: 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-c3b325ef54b74e6fa52a490b8f4de9ef
Source dataset
uspto-grants-2009_04
Patent number
US07517884B2

Reaction notes

Loading…