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+]>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
4
Reactant 2
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- 95 °C
Procedure
A flask was charged successively with 366 mg (1.5 mmol) (S)-2-bromophenylalanine, 217 mg (1.6 mmmol) K2CO3 and 3 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 5 h hour the conversion was approximately 37%. After 22 h full conversion of (S)-2-bromophenylalanine was found. The reaction mixture was cooled to 25° C. and analyzed by HPLC. The yield in solution of (S)-2,3-dihydro-1H-indole-2-carboxylic acid was 95.6%, ee>99%.
Workup
- customThe reactor was flushed with argon
- waitAfter 22 h full conversion of (S)-2-bromophenylalanine was found
- temperatureThe reaction mixture was cooled to 25° C.
Sources & evidence
- ORD record
- ord-c008323dde734113a7325f8fb66c1216
- Source dataset
- uspto-grants-2010_06
- Patent number
- US07732621B2
Reaction notes
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