Aluminum(III) Chloride → (S)-methyl 3-(2-methylpyrrolidin-1-yl)-2-oxo-1,2-dihydroquinoxaline-6-carboxylate
Reaction equation
C([N:8]1[C:17]2[C:12](=[CH:13][C:14]([C:18]([O:20][CH3:21])=[O:19])=[CH:15][CH:16]=2)[N:11]=[C:10]([N:22]2[CH2:26][CH2:25][CH2:24][C@@H:23]2[CH3:27])[C:9]1=[O:28])C1C=CC=CC=1.[Al+3].[Cl-].[Cl-].[Cl-]>ClCCl>[CH3:27][C@H:23]1[CH2:24][CH2:25][CH2:26][N:22]1[C:10]1[C:9](=[O:28])[NH:8][C:17]2[C:12]([N:11]=1)=[CH:13][C:14]([C:18]([O:20][CH3:21])=[O:19])=[CH:15][CH:16]=2Participants
4
Reactant 2
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- 30 °C
Procedure
Into a 250-mL round-bottom flask, was placed a solution of (S)-methyl 1-benzyl-3-(2-methylpyrrolidin-1-yl)-2-oxo-1,2-dihydroquinoxaline-6-carboxylate (2.2 g, 5.84 mmol, 1.00 equiv) in dichloromethane (100 mL). This was followed by the addition of AlCl3 (7.7 g, 58.33 mmol, 10.00 equiv) in several batches. The resulting solution was stirred overnight at 30° C. in an oil bath. The resulting solution was concentrated under vacuum. The residue was applied onto a silica gel column with dichloromethane/methanol (1:100). This resulted in 900 mg (53%) of (S)-methyl 3-(2-methylpyrrolidin-1-yl)-2-oxo-1,2-dihydroquinoxaline-6-carboxylate as a brown solid.
Workup
- customInto a 250-mL round-bottom flask, was placed
- concentrationThe resulting solution was concentrated under vacuum
- customThis resulted in 900 mg (53%) of (S)-methyl 3-(2-methylpyrrolidin-1-yl)-2-oxo-1,2-dihydroquinoxaline-6-carboxylate as a brown solid
Sources & evidence
- ORD record
- ord-3835794abe0e4730a7ca2613ddb2d1f6
- Source dataset
- uspto-grants-2014_12
- Patent number
- US08916560B2
Reaction notes
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