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rac-Ethyl 2-[3-(benzylamino)-4-fluorophenyl]-trans-cyclopropanecarboxylate → rac-Ethyl 2-[3-amino-4-fluorophenyl]-trans-cyclopropanecarboxylate

HRID 1476068
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 1476068
C([NH:8][C:9]1[CH:10]=[C:11]([C@@H:16]2[CH2:18][C@H:17]2[C:19]([O:21][CH2:22][CH3:23])=[O:20])[CH:12]=[CH:13][C:14]=1[F:15])C1C=CC=CC=1.[H][H]>C(O)C.C1COCC1.[Pd]>[NH2:8][C:9]1[CH:10]=[C:11]([C@@H:16]2[CH2:18][C@H:17]2[C:19]([O:21][CH2:22][CH3:23])=[O:20])[CH:12]=[CH:13][C:14]=1[F:15]
KomponentenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion

Komponenten

5

Edukt 2

HCID 123461582rac-Ethyl 2-[3-(benzylamino)-4-fluorophenyl]-trans-cyclopropanecarboxylateHCID 178418361HCID 178418361, Verbindung

Produkt 1

HCID 123637899rac-Ethyl 2-[3-amino-4-fluorophenyl]-trans-cyclopropanecarboxylate

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 23938PalladiumKatalysatorHCID 21873804Tetrahydrofuran ethanol
Lösungsmittel

Versuchsvorschrift

262 mg (purity 66%, 0.55 mmol) of (+/−)-ethyl 2-[3-(benzylamino)-4-fluorophenyl]-trans-cyclopropanecarboxylate were dissolved in 5 ml of ethanol/THF (1:1), 26 mg of palladium on carbon (10%) were added and the mixture was hydrogenated at RT using a hydrogen pressure of 1 bar for 24 h. The reaction mixture was then filtered through celite, the residue was washed with ethanol and the filtrate was concentrated. The crude product obtained in this manner was purified by preparative HPLC. This gave 87 mg (69% of theory) of the target compound.

Aufarbeitung

  1. customwas hydrogenated at RT
  2. customfor 24 h
  3. filtrationThe reaction mixture was then filtered through celite
  4. washthe residue was washed with ethanol
  5. concentrationthe filtrate was concentrated

Quellen und Nachweise

ORD-Eintrag
ord-0395c158f5d54612a9a55dfaa91fc24b
Quelldatensatz
uspto-grants-2015_04
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US09018414B2

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