Phenacyl bromide → 3-((Bis(3-fluorophenyl)methoxy)carbonyl)-1-(2-oxo-2-phenylethyl)-1-azoniabicyclo[2.2.2]octane bromide

HRID 1910499

Reaction equation

HRID 1910499 reaction equation
[N:1]12[CH2:8][CH2:7][CH:4]([CH2:5][CH2:6]1)[CH:3]([C:9]([O:11][CH:12]([C:20]1[CH:25]=[CH:24][CH:23]=[C:22]([F:26])[CH:21]=1)[C:13]1[CH:18]=[CH:17][CH:16]=[C:15]([F:19])[CH:14]=1)=[O:10])[CH2:2]2.[Br:27][CH2:28][C:29]([C:31]1[CH:36]=[CH:35][CH:34]=[CH:33][CH:32]=1)=[O:30]>C(#N)C>[Br-:27].[F:26][C:22]1[CH:21]=[C:20]([CH:12]([C:13]2[CH:18]=[CH:17][CH:16]=[C:15]([F:19])[CH:14]=2)[O:11][C:9]([CH:3]2[CH:4]3[CH2:5][CH2:6][N+:1]([CH2:28][C:29](=[O:30])[C:31]4[CH:36]=[CH:35][CH:34]=[CH:33][CH:32]=4)([CH2:8][CH2:7]3)[CH2:2]2)=[O:10])[CH:25]=[CH:24][CH:23]=1

Participants

4

Reactant 2

HCID 6259Phenacyl bromideHCID 70925896Bis(3-fluorophenyl)methyl quinuclidine-3-carboxylate

Product 1

HCID 866729363-((Bis(3-fluorophenyl)methoxy)carbonyl)-1-(2-oxo-2-phenylethyl)-1-azoniabicyclo[2.2.2]octane bromideYield 73.2%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

Bis(3-fluorophenyl)methyl quinuclidine-3-carboxylate (95 mg, 0.27 mmol, prepared as in example 4) and 2-bromo-1-phenylethanone (58.2 mg, 0.29 mmol) were dissolved in acetonitrile (5 ml) and stirred at room temperature overnight. The solvent was evaporated, and the resulting residue was purified by flash chromatography (DCM/MeOH=95/5 to 9/1) to obtain 3-((bis(3-fluorophenyl)methoxy)carbonyl)-1-(2-oxo-2-phenylethyl)-1-azoniabicyclo[2.2.2]octane bromide (110 mg, racemic mixture).

Workup

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

Sources & evidence

ORD record
ord-56119211b8554d588e5c2f8510d25183
Source dataset
uspto-grants-2013_12
Patent number
US08604015B2

Linked notes

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