Tetrahydrofuran → (R)-4-ethyl-1-[4-(trifluoromethyl)phenyl]-2-azetidinone
Reaction equation
O1CCCC1.[F:6][C:7]([F:27])([F:26])[C:8]1[CH:13]=[CH:12][C:11]([NH:14][C:15](=[O:25])[CH2:16][C@@H:17](OS(C)(=O)=O)[CH2:18][CH3:19])=[CH:10][CH:9]=1.O1CCCC1.C([Mg]Cl)(C)(C)C>O>[CH2:18]([C@H:17]1[N:14]([C:11]2[CH:12]=[CH:13][C:8]([C:7]([F:27])([F:26])[F:6])=[CH:9][CH:10]=2)[C:15](=[O:25])[CH2:16]1)[CH3:19]Participants
Procedure
To a tetrahydrofuran solution (1 mL) containing 200 mg (0.589 mmol) of (S)-N-[4-(trifluoromethyl)phenyl]-3-methanesulfonyloxypentanoic acid amide produced in Example 3, 368.4 mg (0.589 mmol) of tert-butylmagnesium chloride tetrahydrofuran solution (1.6 mmol/g) was added dropwise at room temperature for 5 minutes. After stirring at room temperature for further 2 hours, water (5 mL) was added and extraction was carried out with ethyl acetate. The organic layer was washed with saturated brine and the product was dried with anhydrous sodium sulfate. The solvent was removed by distillation under reduced pressure to obtain (R)-4-ethyl-1-[4-(trifluoromethyl)phenyl]-2-azetidinone as a brown solid (136.4 mg). The reaction yield of the product was determined by the method described in Example 7 to be 61%.
Workup
- additionwas added dropwise at room temperature for 5 minutes
- extractionextraction
- washThe organic layer was washed with saturated brine
- dry with materialthe product was dried with anhydrous sodium sulfate
- customThe solvent was removed by distillation under reduced pressure
Sources & evidence
- ORD record
- ord-9220852978ce4a5ba6841191d5997032
- Source dataset
- uspto-grants-2007_05
- Patent number
- US07223859B2
Reaction notes
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