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

HRID 588336Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 588336
[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-58e38d47f6754cd49f6e6e7fddbc2cd4
Quelldatensatz
uspto-grants-2016_01
Patentnummer
US09227964B2

Notizen zur Reaktion

Wird geladen…