Potassium Carbonate → Indoline-2-carboxylic acid, (S)-
Reaction equation
Br[C:2]1[CH:13]=[CH:12][CH:11]=[CH:10][C:3]=1[CH2:4][C@@H:5]([C:7]([OH:9])=[O:8])[NH2:6].C([O-])([O-])=O.[K+].[K+]>Cl[Cu].O>[NH:6]1[C:10]2[C:3](=[CH:2][CH:13]=[CH:12][CH:11]=2)[CH2:4][C@H:5]1[C:7]([OH:9])=[O:8]Participants
Reactant 2
Product 1
Reagents, catalysts & solvents 2
Conditions
- Temperature
- 95 °C
Procedure
A flask was charged successively with 4.89 g (20.0 mmol) (S)-2-bromophenylalanine, 2.93 g (21.2 mmol) K2CO3, 0.2 mg CuCl (2.9 mmol) and 39.7 g H2O. The reactor was flushed with argon and then kept under a slow stream of argon. The reaction mixture was stirred and heated until 95° C. and kept at this temperature. Samples were taken regularly and analyzed by HPLC. After 4 h hour full conversion of (S)-2-bromophenylalanine was found. The reaction mixture was cooled to 25° C. Then the reaction mixture was acidified with 4.47 g 5M aqueous HCl until pH=4.4. The precipitated (S)-2,3-dihydro-1H-indole-2-carboxylic acid was isolated by filtration and washed with 2×10 mL H2O. Found after drying 2.24 g (13.7 mmol) (S)-2,3-dihydro-1H-indole-2-carboxylic acid. Yield 69%, ee>99%.
Workup
- customThe reactor was flushed with argon
- temperatureThe reaction mixture was cooled to 25° C
Sources & evidence
- ORD record
- ord-4eadd03d57b64ca3904388a9a3414166
- Source dataset
- uspto-grants-2010_06
- Patent number
- US07732621B2
Reaction notes
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