Benzyl Bromide → HCID 86672942, compound

HRID 1910504Notes

Reaction equation

HRID 1910504 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]1[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=1>CCOC(C)=O>[Br-:27].[CH2:28]([N+:1]12[CH2:6][CH2:5][CH:4]([CH2:7][CH2:8]1)[CH:3]([C:9]([O:11][CH:12]([C:13]1[CH:18]=[CH:17][CH:16]=[C:15]([F:19])[CH:14]=1)[C:20]1[CH:25]=[CH:24][CH:23]=[C:22]([F:26])[CH:21]=1)=[O:10])[CH2:2]2)[C:29]1[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=1

Participants

4

Reactant 2

HCID 7498Benzyl BromideHCID 70925896Bis(3-fluorophenyl)methyl quinuclidine-3-carboxylate

Product 1

HCID 86672942HCID 86672942, compoundYield 37.8%

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

To a solution of bis(3-fluorophenyl)methyl quinuclidine-3-carboxylate (90 mg, 0.25 mmol, prepared as in example 4) in EtOAc (3 ml), (bromomethyl)benzene (30.0 μl, 0.25 mmol) was added, and the reaction was stirred at room temperature overnight. The solvent was removed, and the crude was purified by flash chromatography (DCM/MeOH=95/5) to obtain 1-benzyl-3-((bis(3-fluorophenyl)methoxy)carbonyl)-1-azoniabicyclo[2.2.2]octane bromide (50 mg, racemic mixture).

Workup

  1. customThe solvent was removed
  2. customthe crude was purified by flash chromatography (DCM/MeOH=95/5)

Sources & evidence

ORD record
ord-1418eae3a0174f409640a93ce55b10fd
Source dataset
uspto-grants-2013_12
Patent number
US08604015B2

Reaction notes

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