tert-Butyl 1-[3-(benzylamino)-4-chlorobenzyl]cyclopropanecarboxylate → tert-Butyl 1-(3-amino-4-chlorobenzyl)cyclopropanecarboxylate

HRID 626418Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 626418
C([NH:8][C:9]1[CH:10]=[C:11]([CH:23]=[CH:24][C:25]=1[Cl:26])[CH2:12][C:13]1([C:16]([O:18][C:19]([CH3:22])([CH3:21])[CH3:20])=[O:17])[CH2:15][CH2:14]1)C1C=CC=CC=1>C(OCC)(=O)C.[Pd]>[NH2:8][C:9]1[CH:10]=[C:11]([CH:23]=[CH:24][C:25]=1[Cl:26])[CH2:12][C:13]1([C:16]([O:18][C:19]([CH3:22])([CH3:21])[CH3:20])=[O:17])[CH2:14][CH2:15]1

Komponenten

4

Edukt 1

HCID 68006927tert-Butyl 1-[3-(benzylamino)-4-chlorobenzyl]cyclopropanecarboxylate

Produkt 1

HCID 67957815tert-Butyl 1-(3-amino-4-chlorobenzyl)cyclopropanecarboxylate

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 23938PalladiumKatalysatorHCID 8857Ethyl AcetateLösungsmittel

Versuchsvorschrift

50.0 g (134.4 mmol) of tert-butyl 1-[3-(benzylamino)-4-chlorobenzyl]cyclopropanecarboxylate were dissolved in 1.5 liters of ethyl acetate, and 1.43 g (1.34 mmol) of palladium (10% on carbon) were added. The reaction mixture was stirred at RT under a hydrogen atmosphere at standard pressure overnight. The reaction mixture was then filtered off with suction through kieselguhr, and the filtrate was concentrated. The crude product was purified by chromatography on silica gel (mobile phase petroleum ether/ethyl acetate 10:1). The resulting product was stirred in a methanol/water mixture (70:30) and the solid was isolated. 24.3 g (64.1% of theory) of the target compound were obtained.

Aufarbeitung

  1. filtrationThe reaction mixture was then filtered off with suction through kieselguhr
  2. concentrationthe filtrate was concentrated
  3. customThe crude product was purified by chromatography on silica gel (mobile phase petroleum ether/ethyl acetate 10:1)
  4. stirringThe resulting product was stirred in a methanol/water mixture (70:30)
  5. customthe solid was isolated
  6. custom24.3 g (64.1% of theory) of the target compound were obtained

Quellen und Nachweise

ORD-Eintrag
ord-490613a1bcb448629ee3d8bbccaa5500
Quelldatensatz
uspto-grants-2016_04
Patentnummer
US09309198B2

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