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

HRID 588336Notes

Reaction equation

HRID 588336 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-58e38d47f6754cd49f6e6e7fddbc2cd4
Source dataset
uspto-grants-2016_01
Patent number
US09227964B2

Reaction notes

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