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

HRID 2362750Notes

Reaction equation

HRID 2362750 reaction equation
[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

Participants

4

Reactant 2

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

Product 1

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

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

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.

Workup

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

Sources & evidence

ORD record
ord-c739adf40c884835af484faa78f6dc8e
Source dataset
uspto-grants-2014_04
Patent number
US08691840B2

Reaction notes

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