Potassium Carbonate → Indoline-2-carboxylic acid, (S)-

HRID 15493Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 15493
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].CN1C(=O)CCC1>[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]

Komponenten

5

Edukt 2

HCID 11430Potassium CarbonateHCID 1933382-Bromophenylalanine

Produkt 1

HCID 2733920Indoline-2-carboxylic acid, (S)-

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 62652Cuprous chlorideKatalysatorHCID 13387N-methyl-2-pyrrolidoneLösungsmittel

Reaktionsbedingungen

Temperatur
100 °C

Versuchsvorschrift

A flask was charged successively with 366 mg (1.5 mmol) (S)-2-bromophenylalanine, 217 mg (1.6 mmol) K2CO3, 3.2 mg (0.03 mmol) CuCl and 3.2 g NMP. The reactor was flushed with argon and then kept under a slow stream of argon. The reaction mixture was stirred and heated until 100° C. and kept at this temperature. Samples were taken regularly and analyzed by HPLC. After 4 hours, full conversion of (S)-2-bromophenylalanine was found. The yield (measured in solution) of (S)-2,3-dihydro-1H-indole-2-carboxylic acid was 95.9%, ee>98.6%.

Aufarbeitung

  1. customThe reactor was flushed with argon

Quellen und Nachweise

ORD-Eintrag
ord-e52c173020f34d1da676241009458364
Quelldatensatz
uspto-grants-2010_06
Patentnummer
US07732621B2

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