Phenyl Bromoacetate → (R)-3-(2-Fluoro-2,2-diphenyl-acetoxy)-1-phenoxycarbonylmethyl-1-azonia-bicyclo[2.2.2]-octane bromide

HRID 1920555Notes

Reaction equation

HRID 1920555 reaction equation
[N:1]12[CH2:8][CH2:7][CH:4]([CH2:5][CH2:6]1)[C@@H:3]([O:9][C:10](=[O:25])[C:11]([F:24])([C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1)[C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1)[CH2:2]2.[C:26]1([O:32][C:33](=[O:36])[CH2:34][Br:35])[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=1>CS(C)=O>[Br-:35].[F:24][C:11]([C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1)([C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1)[C:10]([O:9][C@@H:3]1[CH:4]2[CH2:5][CH2:6][N+:1]([CH2:34][C:33]([O:32][C:26]3[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=3)=[O:36])([CH2:8][CH2:7]2)[CH2:2]1)=[O:25]

Participants

4

Reactant 2

HCID 564919Phenyl BromoacetateHCID 86611362Fluoro-diphenyl-acetic acid (R)-(1-aza-bicyclo[2.2.2]oct-3-yl)ester

Product 1

HCID 86611363(R)-3-(2-Fluoro-2,2-diphenyl-acetoxy)-1-phenoxycarbonylmethyl-1-azonia-bicyclo[2.2.2]-octane bromide

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent

Procedure

To a solution of fluoro-diphenyl-acetic acid (R)-(1-aza-bicyclo[2.2.2]oct-3-yl) ester [Example 109(i)] (0.034 g, 0.1 mmol) in DMSO (0.25 ml) is added bromo-acetic acid phenyl ester (0.071 ml, 0.5 mmol). The reaction mixture is left standing at room temperature overnight. Purification is carried out by chromatography on C18 silica, eluting with water:acetonitrile to yield the titled compound as a colourless oil.

Workup

  1. waitThe reaction mixture is left
  2. customPurification
  3. washeluting with water

Sources & evidence

ORD record
ord-6502ea9e3feb4bb3af575fb462eb2dfb
Source dataset
uspto-grants-2012_05
Patent number
US08168654B2

Reaction notes

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