Oxalyl chloride → (3R)-Quinuclidine-3-carbonyl chloride hydrochloride

HRID 899172Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 899172
[C:1](Cl)(=O)[C:2]([Cl:4])=[O:3].[N:7]12[CH2:14]C[CH:10]([CH2:11][CH2:12]1)[C@@H:9](C(O)=O)[CH2:8]2>C1(C)C=CC=CC=1>[ClH:4].[N:7]12[CH2:12][CH2:11][CH:10]([CH2:9][CH2:8]1)[C@@H:1]([C:2]([Cl:4])=[O:3])[CH2:14]2

Komponenten

4

Edukt 2

HCID 65578Oxalyl chlorideHCID 1380958(3R)-1-azabicyclo[2.2.2]octane-3-carboxylic acid

Produkt 1

HCID 57462844(3R)-Quinuclidine-3-carbonyl chloride hydrochloride

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 1140TolueneLösungsmittel

Versuchsvorschrift

8.18 g (64.43 mmol) of oxalyl chloride are added dropwise to a solution of 2.0 g (12.89 mmol) of (R)-1-azabicyclo[2.2.2]octane-3-carboxylic acid (Example 3A) in 10 ml of toluene. After stirring at room temperature for 18 h, the reaction mixture is concentrated in vacuo and codistilled with toluene twice. Drying under high vacuum results in 2.31 g (85.2% of theory) of the title compound, which is reacted further without further purification.

Aufarbeitung

  1. concentrationthe reaction mixture is concentrated in vacuo
  2. customDrying under high vacuum

Quellen und Nachweise

ORD-Eintrag
ord-3f1f265e5df84bd2b18b141042a53293
Quelldatensatz
uspto-grants-2008_04
Patentnummer
US07354930B2

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