Hydrochloric Acid → HCID 86743789, Verbindung

HRID 345359Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 345359
[CH2:1]([O:3][C:4]([N:6]1[CH2:10][CH2:9][C@@H:8]([CH2:11][CH:12]=O)[C@@H:7]1[C:14]([O:16][CH2:17][CH3:18])=[O:15])=[O:5])[CH3:2].[Cl-].[CH3:20][O:21]C[P+](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1.CC(C)([O-])C.[K+].O1CCCC1.Cl>O1CCCC1>[CH2:1]([O:3][C:4]([N:6]1[CH2:10][CH2:9][C@@H:8]([CH2:11][CH2:12][CH:20]=[O:21])[C@@H:7]1[C:14]([O:16][CH2:17][CH3:18])=[O:15])=[O:5])[CH3:2]

Komponenten

6

Edukt 4

HCID 313Hydrochloric AcidHCID 2723798Methoxymethyl-triphenylphosphonium chlorideHCID 66863523KOtBu THFHCID 86743787trans 1-Ethoxycarbonyl-2-ethoxycarbonylpyrrolidine-3-acetaldehyde

Produkt 1

HCID 86743789HCID 86743789, Verbindung

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8028TetrahydrofuranLösungsmittel2×

Versuchsvorschrift

To 0.4 g of trans 1-ethoxycarbonyl-2-ethoxycarbonylpyrrolidine-3-acetaldehyde in 5 ml anhydrous tetrahydrofuran under nitrogen, cooled to -78°, is added dropwise a solution of 1.17 g of methoxymethyl-triphenylphosphonium chloride in 15 ml of anhydrous tetrahydrofuran to which is added 1.55 ml of potassium tert-butoxide/tetrahydrofuran (1.6M). Solution is stirred at room temperature for 4 hours. 2N Hydrochloric acid (11 ml) is added and the mixture is stirred for 45 minutes. The solution is concentrated and then extracted with methylene chloride. The extract is dried over sodium sulfate, filtered, concentrated, and the residue is purified by flash chromatography using ethyl acetate/hexane (1:5 to 3:7) to yield trans 1-ethoxycarbonyl-2-ethoxycarbonylpyrrolidine-3-propionaldehyde.

Aufarbeitung

  1. stirringthe mixture is stirred for 45 minutes
  2. concentrationThe solution is concentrated
  3. extractionextracted with methylene chloride
  4. dry with materialThe extract is dried over sodium sulfate
  5. filtrationfiltered
  6. concentrationconcentrated
  7. customthe residue is purified by flash chromatography

Quellen und Nachweise

ORD-Eintrag
ord-d5c2e7d8a4204c229a4f33c275520fec
Quelldatensatz
uspto-grants-1991_10
Patentnummer
US05057506

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