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tert-Butyl 1-[3-(benzylamino)benzyl]cyclopropanecarboxylate → tert-Butyl 1-(3-aminobenzyl)cyclopropanecarboxylate

HRID 877206
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 877206
C([NH:8][C:9]1[CH:10]=[C:11]([CH:23]=[CH:24][CH:25]=1)[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(O)C.C1COCC1.[Pd]>[NH2:8][C:9]1[CH:10]=[C:11]([CH:23]=[CH:24][CH:25]=1)[CH2:12][C:13]1([C:16]([O:18][C:19]([CH3:22])([CH3:20])[CH3:21])=[O:17])[CH2:15][CH2:14]1
KomponentenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion

Komponenten

5

Edukt 1

HCID 58136299tert-Butyl 1-[3-(benzylamino)benzyl]cyclopropanecarboxylate

Produkt 1

HCID 58136514tert-Butyl 1-(3-aminobenzyl)cyclopropanecarboxylate

Reagenzien, Katalysatoren, Lösungsmittel 3

HCID 23938PalladiumKatalysatorHCID 702EthanolLösungsmittelHCID 8028TetrahydrofuranLösungsmittel

Versuchsvorschrift

6.98 g (22.43 mmol) of tert-butyl 1-[3-(benzylamino)benzyl]cyclopropanecarboxylate were dissolved in 50 ml of ethanol and 50 ml of THF, and 0.48 g (0.45 mmol) of palladium (10% on carbon) were added. At RT, the mixture was stirred under an atmosphere of hydrogen at atmospheric pressure for 2 h. The reaction mixture was then filtered off with suction through kieselguhr, the residue was washed with THF and the filtrate was concentrated. The crude product was purified by chromatography on silica gel (mobile phase cyclohexane/ethyl acetate 10:1). This gave 3.66 g (65.9% of theory) of the title compound.

Aufarbeitung

  1. filtrationThe reaction mixture was then filtered off with suction through kieselguhr
  2. washthe residue was washed with THF
  3. concentrationthe filtrate was concentrated
  4. customThe crude product was purified by chromatography on silica gel (mobile phase cyclohexane/ethyl acetate 10:1)

Quellen und Nachweise

ORD-Eintrag
ord-13a73e931b824dd0aa2ac7f5a6310de9
Quelldatensatz
uspto-grants-2015_03
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US08987256B2

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