Formamide → 4-hydroxy-N-methylproline

HRID 9940

Reaktionsgleichung

Reaktionsgleichung von HRID 9940
[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-9c8bc77dc55d4a88890aa30b737c9dda
Quelldatensatz
uspto-grants-2006_08
Patentnummer
US07091363B2

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