4,4'-Ethylenedianiline → N-Boc-pyrrolidine

HRID 71818

Reaktionsgleichung

Reaktionsgleichung von HRID 71818
C(C1C=CC(N)=CC=1)CC1C=CC(N)=CC=1.[C:17]([O:21][C:22]([N:24]1[CH2:28][CH2:27][CH2:26][CH:25]1C(O)=O)=[O:23])([CH3:20])([CH3:19])[CH3:18].C(OC(N1C2C(=CC=CC=2)C=CC1)=O)C>C(Cl)Cl>[C:17]([O:21][C:22]([N:24]1[CH2:28][CH2:27][CH2:26][CH2:25]1)=[O:23])([CH3:20])([CH3:18])[CH3:19]

Komponenten

5

Edukt 3

HCID 121384,4'-EthylenedianilineHCID 278131(2H)-Quinolinecarboxylic acid, ethyl esterHCID 2684721-[(Tert-butoxy)carbonyl]pyrrolidine-2-carboxylic acid

Produkt 1

HCID 643455N-Boc-pyrrolidineAusbeute 147,2 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6344DichloromethaneLösungsmittel

Versuchsvorschrift

4,4′-Ethylenedianiline (2.98 g) and pyrrolidine-1,2-dicarboxylic acid 1-tert-butyl ester (7.09 g) were dissolved in DCM (90 mL), and 1-ethoxycarbonyl-1,2-dihydroquinoline (8.38 g) was added. The reaction mixture was stirred at ambient temperature for 3 hours and evaporated under vacuum. Oil was dissolved in ethyl acetate, forming a precipitate, which was collected by vacuum filtration and dried under vacuum, giving 2-[4-(2-{4-[(1-carboxylic acid tert-butyl ester-pyrrolidine-2-carbonyl)-amino]-phenyl}-ethyl)-phenylcarbamoyl]-pyrrolidine-1-carboxylic acid tert-butyl ester (8.30 g, 97%) as a white solid.

Aufarbeitung

  1. customevaporated under vacuum
  2. dissolutionOil was dissolved in ethyl acetate
  3. customforming a precipitate, which
  4. filtrationwas collected by vacuum filtration
  5. customdried under vacuum

Quellen und Nachweise

ORD-Eintrag
ord-8e6ab336506e46f299ab7342315879df
Quelldatensatz
uspto-grants-2014_09
Patentnummer
US08822430B2

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