(2R,4R)-4-Azido-2-hydroxymethyl-pyrrolidine-1-carboxylic acid tert-butyl ester → tert-butyl (2R,4R)-4-amino-2-(hydroxymethyl)pyrrolidine-1-carboxylate

HRID 244350Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 244350
[C:1]([O:5][C:6]([N:8]1[CH2:12][C@H:11]([N:13]=[N+]=[N-])[CH2:10][C@@H:9]1[CH2:16][OH:17])=[O:7])([CH3:4])([CH3:3])[CH3:2].[H][H]>[Pd].CO>[C:1]([O:5][C:6]([N:8]1[CH2:12][C@H:11]([NH2:13])[CH2:10][C@@H:9]1[CH2:16][OH:17])=[O:7])([CH3:4])([CH3:3])[CH3:2]

Komponenten

5

Edukt 2

HCID 58564434(2R,4R)-4-Azido-2-hydroxymethyl-pyrrolidine-1-carboxylic acid tert-butyl esterHCID 178418361HCID 178418361, Verbindung

Produkt 1

HCID 45072438tert-butyl (2R,4R)-4-amino-2-(hydroxymethyl)pyrrolidine-1-carboxylateAusbeute 98,4 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 23938PalladiumKatalysatorHCID 887MethanolLösungsmittel

Versuchsvorschrift

Hydrogenate a mixture of (2R,4R)-4-azido-2-hydroxymethyl-pyrrolidine-1-carboxylic acid tert-butyl ester (225 g, 0.93 mol) and 10% palladium on carbon (22.5 g, pre-wetted with toluene) in methanol (2.3 L) at 15 psi of hydrogen at room temperature for 16 h. Filter off the catalyst and concentrate the filtrate to obtain the title compound as an oil (198 g, 92%). 1H NMR (400 MHz, DMSO-d6) δ 1.38 (s, 9H), 1.58 (m, 1H), 2.16 (m, 1H), 2.95 (m, 1H), 3.20-3.58 (m, 6H), 3.61 (m, 1H), 3.65 (br s, 1H).

Aufarbeitung

  1. filtrationFilter off the catalyst
  2. concentrationconcentrate the filtrate

Quellen und Nachweise

ORD-Eintrag
ord-7fb19b96761747ba93f21083070bb514
Quelldatensatz
uspto-grants-2014_02
Patentnummer
US08658638B2

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