Salicylaldehyde → 3-Hydroxy-3-{1-[(2-hydroxybenzylidene)amino]ethyl}pyrrolidine-1-carboxylic acid benzyl ester

HRID 10350

Reaktionsgleichung

Reaktionsgleichung von HRID 10350
[CH2:1]([O:8][C:9]([N:11]1[CH2:15][CH2:14][C:13]([CH:17]([NH2:19])[CH3:18])([OH:16])[CH2:12]1)=[O:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[CH:20](=O)[C:21]1[C:22](=[CH:24][CH:25]=[CH:26][CH:27]=1)[OH:23]>C(O)C>[CH2:1]([O:8][C:9]([N:11]1[CH2:15][CH2:14][C:13]([OH:16])([CH:17]([N:19]=[CH:20][C:21]2[CH:27]=[CH:26][CH:25]=[CH:24][C:22]=2[OH:23])[CH3:18])[CH2:12]1)=[O:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Komponenten

4

Edukt 2

HCID 6998SalicylaldehydeHCID 690686403-(1-Aminoethyl)-3-hydroxypyrrolidine-1-carboxylic acid benzyl ester

Produkt 1

HCID 1363303273-Hydroxy-3-{1-[(2-hydroxybenzylidene)amino]ethyl}pyrrolidine-1-carboxylic acid benzyl esterAusbeute 35 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 702EthanolLösungsmittel

Versuchsvorschrift

A solution of 3-(1-aminoethyl)-3-hydroxypyrrolidine-1-carboxylic acid benzyl ester (Example A10, 0.34 g, 0.93 mmol) and salicylaldehyde (0.147 g, 1.2 mmol) in dry ethanol (5 mL) is refluxed for 3 hours. After evaporation of the solvent, the residue is purified by column chromatography (30:70:0.01 ethyl acetate/hexanes/ammonium hydroxide) to afford the title compound (0.12 g). 1H NMR (200 MHz, CDCl3): δ 8.39 (s, 1H), 7.41–7.25 (m, 7H), 6.97–6.85 (m, 2H), 5.09 (s, 2H), 3.65–3.34 (m, 5H), 2.01–1.87 (m, 2H), 1.37–1.32 (m, 3H).

Aufarbeitung

  1. customis refluxed for 3 hours
  2. customAfter evaporation of the solvent
  3. customthe residue is purified by column chromatography (30:70:0.01 ethyl acetate/hexanes/ammonium hydroxide)

Quellen und Nachweise

ORD-Eintrag
ord-59aeace69c524501960f8f1eb266305a
Quelldatensatz
uspto-grants-2006_08
Patentnummer
US07094780B1

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