4-Chloroaniline → tert-butyl (R)-2-(4-chlorophenylcarbamoyl)pyrrolidine-1-carboxylate

HRID 602342

Reaktionsgleichung

Reaktionsgleichung von HRID 602342
C(OC1C=CC2C(=CC=CC=2)N1C(OCC)=O)C.[C:19]([N:26]1[CH2:33][CH2:32][CH2:31][C@@H:27]1[C:28]([OH:30])=O)([O:21][C:22]([CH3:25])([CH3:24])[CH3:23])=[O:20].[Cl:34][C:35]1[CH:41]=[CH:40][C:38]([NH2:39])=[CH:37][CH:36]=1>C1(C)C=CC=CC=1>[Cl:34][C:35]1[CH:41]=[CH:40][C:38]([NH:39][C:28]([C@H:27]2[CH2:31][CH2:32][CH2:33][N:26]2[C:19]([O:21][C:22]([CH3:23])([CH3:24])[CH3:25])=[O:20])=[O:30])=[CH:37][CH:36]=1

Komponenten

5

Edukt 3

HCID 78124-ChloroanilineHCID 278332-Ethoxy-1-(ethoxycarbonyl)-1,2-dihydroquinolineHCID 688022(2R)-1-[(tert-butoxy)carbonyl]pyrrolidine-2-carboxylic acid

Produkt 1

HCID 9138711tert-butyl (R)-2-(4-chlorophenylcarbamoyl)pyrrolidine-1-carboxylate

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 1140TolueneLösungsmittel

Versuchsvorschrift

4.82 g (19.5 mmol) of ethyl 2-ethoxy-1,2-dihydroquinoline-1-carboxylate (EEDQ) are added to a suspension of 2.80 g (13.0 mmol) of N-Boc-D-proline and 1.66 g (13.0 mmol) of 4-chloroaniline in 50 ml of toluene, and the mixture is stirred at room temperature for 3 hours. The reaction mixture is filtered, and petroleum ether is added to the filtrate. The precipitate formed is filtered off and dried, giving tert-butyl (R)-2-(4-chlorophenylcarbamoyl)pyrrolidine-1-carboxylate as colourless crystals; ESI 325.

Aufarbeitung

  1. filtrationThe reaction mixture is filtered
  2. additionpetroleum ether is added to the filtrate
  3. customThe precipitate formed
  4. filtrationis filtered off
  5. customdried

Quellen und Nachweise

ORD-Eintrag
ord-3d4be8b56c6e4a41abd341a00e524224
Quelldatensatz
uspto-grants-2011_03
Patentnummer
US07906516B2

Verknüpfte Notizen

Wird geladen…