HCID 67406569, Verbindung → HCID 67406325, Verbindung

HRID 1372625Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1372625
C([O:8][CH2:9]/[CH:10]=[CH:11]\[CH2:12][O:13][CH2:14][C@@H:15]1[CH2:19][C@H:18]([F:20])[CH2:17][N:16]1[C:21]([O:23][C:24]([CH3:27])([CH3:26])[CH3:25])=[O:22])C1C=CC=CC=1>C(O)C.[OH-].[Pd+2].[OH-]>[C:24]([O:23][C:21]([N:16]1[CH2:17][C@@H:18]([F:20])[CH2:19][C@H:15]1[CH2:14][O:13][CH2:12][CH2:11][CH2:10][CH2:9][OH:8])=[O:22])([CH3:27])([CH3:26])[CH3:25]

Komponenten

4

Edukt 1

HCID 67406569HCID 67406569, Verbindung

Produkt 1

HCID 67406325HCID 67406325, VerbindungAusbeute 68,6 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 9942167Palladium hydroxideKatalysatorHCID 702EthanolLösungsmittel

Versuchsvorschrift

In ethanol (200 ml) were suspended (Z)-(2S,4S)-2-(4-benzyloxy-2-butenyloxymethyl)-1-(tert-butoxycarbonyl)-4-fluoropyrrolidine (4.58 g, 12.1 mmol) and 20% palladium hydroxide (4.0 g). The resulting suspension was subjected to catalytic hydrogenation at room temperature under normal pressure for 14 hours. The catalyst was then filtered off and the filtrate was distilled under reduced pressure to remove the solvent. The residue was purified by chromatography on a silica gel column (silica gel: 100 g), whereby from chloroform/acetone (10/1) eluate fractions, the title compound (2.42 g, 67%) was obtained as a colorless oil.

Aufarbeitung

  1. filtrationThe catalyst was then filtered off
  2. distillationthe filtrate was distilled under reduced pressure
  3. customto remove the solvent
  4. customThe residue was purified by chromatography on a silica gel column (silica gel: 100 g), whereby from chloroform/acetone (10/1) eluate fractions

Quellen und Nachweise

ORD-Eintrag
ord-1241dc4f90d44816bd17b9d4d852b94a
Quelldatensatz
uspto-grants-2007_01
Patentnummer
US07157487B2

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