Réaction #43771

ord-e52c173020f34d1da676241009458364

Équation de réaction

N[C@@H](Cc1ccccc1Br)C(=O)O
(S)-2-bromophenylalanine
O=C([O-])[O-].[K+].[K+]
K2CO3
O=C(O)[C@@H]1Cc2ccccc2N1
(S)-2,3-dihydro-1H-indole-2-carboxylic acid

Solvants

Conditions de réaction

Température
100°CELSIUS
Conditions détaillées
See reaction.notes.procedure_details.

Traitement

  1. 1
    AutreThe reactor was flushed with argon

Mode opératoire

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%.

Source

DOI: 10.6084/m9.figshare.5104873.v1Brevet: US07732621B2uspto-grants-2010_06