3-Quinuclidinol, (-)- → (R)-3-Hydroxy-1-(isoxazol-3-ylcarbamoylmethyl)-1-azonia-bicyclo[2.2.2]octane bromide

HRID 2240291Notes

Reaction equation

HRID 2240291 reaction equation
[Br:1][CH2:2][C:3]([NH:5][C:6]1[CH:10]=[CH:9][O:8][N:7]=1)=[O:4].[N:11]12[CH2:18][CH2:17][CH:14]([CH2:15][CH2:16]1)[C@@H:13]([OH:19])[CH2:12]2>C(Cl)(Cl)Cl.C(#N)C>[Br-:1].[OH:19][C@@H:13]1[CH:14]2[CH2:17][CH2:18][N+:11]([CH2:2][C:3](=[O:4])[NH:5][C:6]3[CH:10]=[CH:9][O:8][N:7]=3)([CH2:16][CH2:15]2)[CH2:12]1

Participants

4

Reactant 2

HCID 914043-Quinuclidinol, (-)-HCID 133629192-bromo-N-(isoxazol-3-yl)acetamide

Product 1

HCID 86627857(R)-3-Hydroxy-1-(isoxazol-3-ylcarbamoylmethyl)-1-azonia-bicyclo[2.2.2]octane bromide

Reagents, catalysts & solvents 1

HCID 22555007Acetonitrile chloroformSolvent

Procedure

A solution comprising 2-bromo-N-isoxazol-3-yl-acetamide (0.975 g, 4.72 mmol), (R)-1-aza-bicyclo[2.2.2]octan-3-ol (0.549 g, 4.32 mmol) in chloroform/acetonitrile (1:1) (10 ml) is stirred at room temperature for 30 minutes. The resultant precipitate is filtered, washed with chloroform/acetonitrile (1:1) and dried under vacuum to yield the titled compound as a white solid.

Workup

  1. filtrationThe resultant precipitate is filtered
  2. washwashed with chloroform/acetonitrile (1:1)
  3. customdried under vacuum

Sources & evidence

ORD record
ord-0e0d45716d9c46fd86151f7476190862
Source dataset
uspto-grants-2010_05
Patent number
US07723356B2

Reaction notes

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