Styrene → 4-[2-((1E)-2-Phenylvinyl)-4-chlorophenyl](4R)pyrrolidin-2-one
Reaction equation
Br[C:2]1[CH:7]=[C:6]([Cl:8])[CH:5]=[CH:4][C:3]=1[C@@H:9]1[CH2:13][NH:12][C:11](=[O:14])[CH2:10]1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.[CH2:34]=[CH:35][C:36]1[CH:41]=[CH:40][CH:39]=[CH:38][CH:37]=1.C(N(C(C)C)CC)(C)C>CN(C=O)C.Cl.CC([O-])=O.CC([O-])=O.[Pd+2]>[C:36]1(/[CH:35]=[CH:34]/[C:2]2[CH:7]=[C:6]([Cl:8])[CH:5]=[CH:4][C:3]=2[C@@H:9]2[CH2:13][NH:12][C:11](=[O:14])[CH2:10]2)[CH:41]=[CH:40][CH:39]=[CH:38][CH:37]=1Participants
8
Reactant 4
Product 1
Reagents, catalysts & solvents 3
Conditions
- Temperature
- 90 °C
Procedure
To a solution of (4R)-4-(2-bromo-4-chlorophenyl)pyrrolidin-2-one (140 mg, 0.51 mmol), Pd(OAc)2 (34 mg, 0.15 mmol) and triphenylphosphine (0.3 mmol) in DMF (1 mL) was added styrene (0.17 mL, 2 mmol) followed by diisopropylethylamine (0.17 mL, 1.02 mmol) under a N2 atmosphere. The reaction mixture was heated to 90° C. overnight. The mixture was then cooled to room temperature and diluted with 1N HCl aq. solution (10 mL) and extracted with ethyl acetate (3×30 mL). The combined organic phases were washed with brine (3×30 mL) and dried over MgSO4. The solvent was removed in vacuo to provide 4-[2-((1E)-2-phenylvinyl)-4-chlorophenyl](4R)pyrrolidin-2-one (3a) (120 mg). MS (ESI) m/z 284.02 (M+H)+.
Workup
- temperatureThe mixture was then cooled to room temperature
- extractionextracted with ethyl acetate (3×30 mL)
- washThe combined organic phases were washed with brine (3×30 mL)
- dry with materialdried over MgSO4
- customThe solvent was removed in vacuo
Sources & evidence
- ORD record
- ord-8615d8985e574542ab82005c8f1f2dd7
- Source dataset
- uspto-grants-2013_01
- Patent number
- US08344028B2
Reaction notes
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