2,4-Dihydroxybenzaldehyde → 4-[((3S)-1-tert-butoxycarbonyl-3-pyrrolidinyl)oxy]-2-hydroxybenzaldehyde

HRID 53999

Reaktionsgleichung

Reaktionsgleichung von HRID 53999
[OH:1][C:2]1[CH:9]=[C:8]([OH:10])[CH:7]=[CH:6][C:3]=1[CH:4]=[O:5].[C:11]([O:15][C:16]([N:18]1[CH2:22][CH2:21][C@@H:20](O)[CH2:19]1)=[O:17])([CH3:14])([CH3:13])[CH3:12].N(C(OCC)=O)=NC(OCC)=O>O1CCCC1>[C:11]([O:15][C:16]([N:18]1[CH2:22][CH2:21][C@H:20]([O:10][C:8]2[CH:7]=[CH:6][C:3]([CH:4]=[O:5])=[C:2]([OH:1])[CH:9]=2)[CH2:19]1)=[O:17])([CH3:14])([CH3:12])[CH3:13]

Komponenten

5

Edukt 3

HCID 72132,4-DihydroxybenzaldehydeHCID 220568ethyl N-ethoxycarbonyliminocarbamateHCID 6544479tert-Butyl (3R)-3-hydroxypyrrolidine-1-carboxylate

Produkt 1

HCID 570351144-[((3S)-1-tert-butoxycarbonyl-3-pyrrolidinyl)oxy]-2-hydroxybenzaldehydeAusbeute 39,1 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8028TetrahydrofuranLösungsmittel

Versuchsvorschrift

in 40 ml of tetrahydrofuran were dissolved 1.38 g of 2,4-dihydroxybenzaldehyde, 1.87 g of (3R)-1-tert-butoxycarbonyl-3-hydroxypyrrolidine and 2.88 g of triphenylphosphone. The thus prepared solution was mixed with 1.91 g of diethyl azodicarboxylate and stirred at room temperature for 1 hour. After distilling off the solvent, the resulting residue was purified by subjecting it to silica gel column chromatography, thereby obtaining 1.2 g of 4-[((3S)-1-tert-butoxycarbonyl-3-pyrrolidinyl)oxy]-2-hydroxybenzaldehyde in a viscous and oily form.

Aufarbeitung

  1. distillationAfter distilling off the solvent
  2. customthe resulting residue was purified

Quellen und Nachweise

ORD-Eintrag
ord-df11f5c2e534419381a6e2930bd28079
Quelldatensatz
uspto-grants-1997_04
Patentnummer
US05620991

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