N-acetyl-4-azido-2-hydroxymethylpyrrolidine → 1-((2S,4S)-4-Amino-2-(hydroxymethyl)pyrrolidin-1-yl)ethanone

HRID 1723903Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1723903
[C:1]([N:4]1[CH2:8][CH:7]([N:9]=[N+]=[N-])[CH2:6][CH:5]1[CH2:12][OH:13])(=[O:3])[CH3:2].[H][H]>[Pd].CO>[C:1]([N:4]1[CH2:8][C@@H:7]([NH2:9])[CH2:6][C@H:5]1[CH2:12][OH:13])(=[O:3])[CH3:2]

Komponenten

5

Edukt 2

HCID 23078017N-acetyl-4-azido-2-hydroxymethylpyrrolidineHCID 178418361HCID 178418361, Verbindung

Produkt 1

HCID 450861111-((2S,4S)-4-Amino-2-(hydroxymethyl)pyrrolidin-1-yl)ethanoneAusbeute 89,6 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 23938PalladiumKatalysatorHCID 887MethanolLösungsmittel

Versuchsvorschrift

92.4 g of 10% Pd—C was added to a solution of 534 g of N-acetyl-4-azido-2-hydroxymethylpyrrolidine and 2.6 L of methanol, and this was hydrogenated (30 hours) at a normal pressure until the raw material disappeared, while the atmosphere in the container was substituted for hydrogen gas every one hour. After filtration, the solution was concentrated under reduced pressure to obtain 411 g of (2S, 4S)-N-acetyl-4-amino-2-hydroxymethylpyrrolidine, more specifically, (2S,4S)-(−)-1-acetyl-4-amino-2-hydroxymethyl-pyrrolidine as an oil.

Aufarbeitung

  1. customthis was hydrogenated (30 hours)
  2. filtrationAfter filtration
  3. concentrationthe solution was concentrated under reduced pressure

Quellen und Nachweise

ORD-Eintrag
ord-143e67eac0974e3298c6e852043e833f
Quelldatensatz
uspto-grants-2009_02
Patentnummer
US07485665B2

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