Formamide → 4-hydroxy-N-methylproline

HRID 1797450Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1797450
[CH2:1]1[C@@H:5]([C:6]([OH:8])=[O:7])[NH:4][CH2:3][C@@H:2]1[OH:9].[CH:10](N)=O.[H][H]>[Pd].O.C(O)C>[OH:9][C@H:2]1[CH2:3][N:4]([CH3:10])[C@H:5]([C:6]([OH:8])=[O:7])[CH2:1]1

Komponenten

7

Edukt 3

HCID 713FormamideHCID 5810L-HydroxyprolineHCID 178418361HCID 178418361, Verbindung

Produkt 1

HCID 117687004-hydroxy-N-methylprolineAusbeute 92,1 %

Reagenzien, Katalysatoren, Lösungsmittel 3

HCID 23938PalladiumKatalysatorHCID 702EthanolLösungsmittelHCID 962WaterLösungsmittel

Versuchsvorschrift

A suspension of (2S,4R)-trans-4-hydroxyproline (5 g), 37% aqueous formamide solution (4.6 g) and 7.5% palladium on charcoal (53% water content, 3.2 g) in water (15 mL) was stirred at room temperature in an atmosphere of high-pressure hydrogen for 10 hours. After removing the palladium on charcoal by filtration, the water of the filtrate was removed by distillation under reduced pressure. The solid residue thus obtained was suspended and stirred in ethanol (25 mL). The crystals which precipitated were collected by filtration to give the title compound (5.1 g, yield 92%).

Aufarbeitung

  1. customAfter removing the palladium on charcoal
  2. filtrationby filtration
  3. customthe water of the filtrate was removed by distillation under reduced pressure
  4. customThe solid residue thus obtained
  5. customThe crystals which precipitated
  6. filtrationwere collected by filtration

Quellen und Nachweise

ORD-Eintrag
ord-99879703f591419ba749944fe22ceb49
Quelldatensatz
uspto-grants-2006_04
Patentnummer
US07034150B2

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