2-Bromo-1-(1,3-thiazol-2-yl)ethan-1-one → (3R)-1-(2-oxo-2-(thiazol-2-yl)ethyl)-3-(2-phenyl-2-(piperidin-1-yl)acetoxy)-1-azoniabicyclo[2.2.2]octane bromide

HRID 404617Notes

Reaction equation

HRID 404617 reaction equation
[C:1]1([CH:7]([N:19]2[CH2:24][CH2:23][CH2:22][CH2:21][CH2:20]2)[C:8]([O:10][C@@H:11]2[CH:16]3[CH2:17][CH2:18][N:13]([CH2:14][CH2:15]3)[CH2:12]2)=[O:9])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[Br:25][CH2:26][C:27]([C:29]1[S:30][CH:31]=[CH:32][N:33]=1)=[O:28]>C(OCC)(=O)C>[Br-:25].[O:28]=[C:27]([C:29]1[S:30][CH:31]=[CH:32][N:33]=1)[CH2:26][N+:13]12[CH2:18][CH2:17][CH:16]([CH2:15][CH2:14]1)[C@@H:11]([O:10][C:8](=[O:9])[CH:7]([C:1]1[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1)[N:19]1[CH2:24][CH2:23][CH2:22][CH2:21][CH2:20]1)[CH2:12]2

Participants

4

Reactant 2

HCID 27952122-Bromo-1-(1,3-thiazol-2-yl)ethan-1-oneHCID 71603247(R)-quinuclidin-3-yl 2-phenyl-2-(piperidin-1-yl)acetate

Product 1

HCID 86688877(3R)-1-(2-oxo-2-(thiazol-2-yl)ethyl)-3-(2-phenyl-2-(piperidin-1-yl)acetoxy)-1-azoniabicyclo[2.2.2]octane bromideYield 65%

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

(R)-Quinuclidin-3-yl 2-phenyl-2-(piperidin-1-yl)acetate (120 mg, 0.36 mmol) was dissolved in ethyl acetate (3.65 ml) and 2-bromo-1-(thiazol-2-yl)ethanone (83 mg, 0.42 mmol) was added. The mixture was stirred at room temperature for 16 hours. The solvent was evaporated and the residue was purified by flash chromatography (DCM/MeOH=95/5 to 9/1) to obtain (3R)-1-(2-oxo-2-(thiazol-2-yl)ethyl)-3-(2-phenyl-2-(piperidin-1-yl)acetoxy)-1-azoniabicyclo[2.2.2]octane bromide (125 mg, 0.234 mmol, 64.0% yield) pale brown solid.

Workup

  1. customThe solvent was evaporated
  2. customthe residue was purified by flash chromatography (DCM/MeOH=95/5 to 9/1)

Sources & evidence

ORD record
ord-183e858f2a324bacbd4fc4b0b82adf68
Source dataset
uspto-grants-2014_06
Patent number
US08748613B2

Reaction notes

Loading…