7-Oxa-3-azabicyclo[4.1.0]heptan-3-yl(phenyl)methanone → HCID 54054374, compound
Reaction equation
[C:1]([Mg]Cl)#[CH:2].[O:5]1[CH:11]2[CH:6]1[CH2:7][N:8]([C:12](=[O:19])[C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1)[CH2:9][CH2:10]2>C1COCC1.OS(O)(=O)=O>[C:12]([N:8]1[CH2:9][CH2:10][CH:11]([OH:5])[CH:6]([C:1]#[CH:2])[CH2:7]1)(=[O:19])[C:13]1[CH:14]=[CH:15][CH:16]=[CH:17][CH:18]=1Participants
5
Reactant 2
Product 1
Reagents, catalysts & solvents 2
Conditions
- Temperature
- 5 °C
Procedure
To a solution of ethynyl magnesium chloride in THF (5 mmole) at 0° C., is added dropwise a solution of 40 (5.8 mmole) in THF. The mixture is allowed to stir at 0-10° C. for 1 hour, then at room temperature for an additional hour and then heated with gentle reflux for 30 mm. The reaction mixture is added to ice-water and the formed precipitate, Mg(OH)2, is dissolved in 30% H2SO4. The product formed is extracted repeatedly with methylene chloride. Standard work-up and flash chromatography affords 54.
Workup
- waitat room temperature for an additional hour
- temperatureheated
- temperaturewith gentle reflux for 30 mm
- customThe product formed
- extractionis extracted repeatedly with methylene chloride
Sources & evidence
- ORD record
- ord-2611be6a27f44681a8e6bc8fe4e6d228
- Source dataset
- uspto-grants-1999_07
- Patent number
- US05919797
Reaction notes
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