Cesium carbonate → (2R)-6-[3-(2-methylpyrrolidin-1-yl)propoxy]-3,4-dihydroquinolin-2(1H)-one
Reaction equation
[OH:1][C:2]1[CH:3]=[C:4]2[C:9](=[CH:10][CH:11]=1)[NH:8][C:7](=[O:12])[CH2:6][CH2:5]2.C(=O)([O-])[O-].[Cs+].[Cs+].Cl[CH2:20][CH2:21][CH2:22][N:23]1[CH2:27][CH2:26][CH2:25][C@H:24]1[CH3:28]>C(#N)C.O>[CH3:28][C@@H:24]1[CH2:25][CH2:26][CH2:27][N:23]1[CH2:22][CH2:21][CH2:20][O:1][C:2]1[CH:3]=[C:4]2[C:9](=[CH:10][CH:11]=1)[NH:8][C:7](=[O:12])[CH2:6][CH2:5]2Participants
6
Reactant 3
Product 1
Reagents, catalysts & solvents 2
Conditions
- Temperature
- 100 °C
Procedure
To a solution of 6-hydroxy-3,4-dihydroquinolin-2(1H)-one (0.55 g) in acetonitrile (10 mL), cesium carbonate (2.0 g) and (2R)-1-(3-chloropropyl)-2-methylpyrrolidine prepared in Example 1-(1) (0.50 g) were added and stirred at 100° C. for 1 hour. The reaction mixture was diluted with water and extracted with ethyl acetate. The organic layer was dried over anhydrous magnesium sulfate and concentrated under reduced pressure, and the resulting residue was purified by NH-type silica gel column chromatography (eluting solvent: n-hexane/ethyl acetate=1/1). The resulting solid was subjected to recrystallization from n-hexane to give the titled compound (0.33 g, 37%) as a colorless powder.
Workup
- additionwere added
- extractionextracted with ethyl acetate
- dry with materialThe organic layer was dried over anhydrous magnesium sulfate
- concentrationconcentrated under reduced pressure
- customthe resulting residue was purified by NH-type silica gel column chromatography (eluting solvent: n-hexane/ethyl acetate=1/1)
- customThe resulting solid was subjected to recrystallization from n-hexane
Sources & evidence
- ORD record
- ord-51e38875e7eb4754938dc2d2fb2dc35b
- Source dataset
- uspto-grants-2013_12
- Patent number
- US08609847B2
Reaction notes
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