Cesium carbonate → HCID 70664333, compound
Reaction equation
[OH:1][C@H:2]1[CH2:6][CH2:5][NH:4][C:3]1=[O:7].Br[C:9]1[CH:10]=[C:11]([CH3:15])[CH:12]=[CH:13][CH:14]=1.C1(P(C2C=CC=CC=2)C2C3OC4C(=CC=CC=4P(C4C=CC=CC=4)C4C=CC=CC=4)C(C)(C)C=3C=CC=2)C=CC=CC=1.C(=O)([O-])[O-].[Cs+].[Cs+]>O1CCOCC1.C([O-])(=O)C.[Pd+2].C([O-])(=O)C>[OH:1][C@H:2]1[CH2:6][CH2:5][N:4]([C:9]2[CH:14]=[CH:13][CH:12]=[C:11]([CH3:15])[CH:10]=2)[C:3]1=[O:7]Participants
Reactant 4
Product 1
Reagents, catalysts & solvents 2
Conditions
- Temperature
- 80 °C
Procedure
(S)-3-Hydroxypyrrolidin-2-one (1.52 g, 15.0 mmol), 3-bromotoluene (2.57 g, 15.0 mmol), 4,5-bis(diphenylphosphino)-9,9-dimethylxanthene (0.26 g, 0.45 mmol), palladium(II) acetate (0.067 g, 0.30 mmol) and cesium carbonate (7.33 g, 22.5 mmol) were mixed together in dioxane (50 mL) and stirred overnight at 80° C. overnight. The reaction mixture was washed with water (150 mL), and the aqueous layer was extracted with dichloromethane (3×150 mL). The combined organic layers were dried (sodium sulfate) and concentrated in vacuo. Chromatography over silica gel, eluting with hexanes/ethyl acetate, afforded the title compound as a white solid. 1H NMR (500 MHz, CDCl3) δ 7.47 (s, 1H), 7.42 (d, J=8.3 Hz, 1H), 7.26 (t, J=7.9 Hz, 1H), 7.00 (d, J=7.6 Hz, 1H), 4.81 (d, J=3.1 Hz, 1H), 4.56-4.49 (m, 1H), 3.80-3.70 (m, 2H), 2.60-2.53 (m, 1H), 2.37 (s, 3H), 2.16-2.06 (m, 1H).
Workup
- washThe reaction mixture was washed with water (150 mL)
- extractionthe aqueous layer was extracted with dichloromethane (3×150 mL)
- dry with materialThe combined organic layers were dried (sodium sulfate)
- concentrationconcentrated in vacuo
- washChromatography over silica gel, eluting with hexanes/ethyl acetate
Sources & evidence
- ORD record
- ord-1ba2c6885ce74743a95beecdfdb5dbdd
- Source dataset
- uspto-grants-2013_01
- Patent number
- US08361994B2
Reaction notes
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