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

HRID 1920556Notes

Reaction equation

HRID 1920556 reaction equation
[Br-:1].[F:2][C:3]([C:31]1[CH:36]=[CH:35][CH:34]=[CH:33][CH:32]=1)([C:25]1[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=1)[C:4]([O:6][C@@H:7]1[CH:12]2[CH2:13][CH2:14][N+:9]([CH2:15][C:16](OC3C=CC=CC=3)=[O:17])([CH2:10][CH2:11]2)[CH2:8]1)=[O:5].[C:37]1([O:43]C(=O)C[Br:46])C=CC=C[CH:38]=1>>[Br-:46].[F:2][C:3]([C:25]1[CH:26]=[CH:27][CH:28]=[CH:29][CH:30]=1)([C:31]1[CH:32]=[CH:33][CH:34]=[CH:35][CH:36]=1)[C:4]([O:6][C@@H:7]1[CH:12]2[CH2:13][CH2:14][N+:9]([CH2:15][C:16]#[CH:37])([CH2:10][CH2:11]2)[CH2:8]1)=[O:5].[Br-:1].[C:37]([O:17][CH2:16][CH2:15][N+:9]12[CH2:10][CH2:11][CH:12]([CH2:13][CH2:14]1)[C@@H:7]([O:6][C:4](=[O:5])[C:3]([F:2])([C:25]1[CH:26]=[CH:27][CH:28]=[CH:29][CH:30]=1)[C:31]1[CH:36]=[CH:35][CH:34]=[CH:33][CH:32]=1)[CH2:8]2)(=[O:43])[CH3:38]

Participants

4

Reactant 2

HCID 564919Phenyl BromoacetateHCID 86611363(R)-3-(2-Fluoro-2,2-diphenyl-acetoxy)-1-phenoxycarbonylmethyl-1-azonia-bicyclo[2.2.2]-octane bromide

Product 2

HCID 67496806(R)-1-(2-Acetoxy-ethyl)-3-(2-fluoro-2,2-diphenyl-acetoxy)-1-azonia-bicyclo[2.2.2]octane bromideHCID 86611365(R)-3-(2-Fluoro-2,2-diphenyl-acetoxy)-1-prop-2-ynyl-1-azonia-bicyclo[2.2.2]octane bromide

Procedure

These compounds, namely (R)-3-(2-Fluoro-2,2-diphenyl-acetoxy)-1-prop-2-ynyl-1-azonia-bicyclo[2.2.2]octane bromide and (R)-1-(2-Acetoxy-ethyl)-3-(2-fluoro-2,2-diphenyl-acetoxy)-1-azonia-bicyclo[2.2.2]octane bromide are prepared by an analogous method to (R)-3-(2-fluoro-2,2-diphenyl-acetoxy)-1-phenoxycarbonylmethyl-1-azonia-bicyclo[2.2.2]octane bromide (Example 109) by replacing bromo-acetic acid phenyl ester with the appropriate alkyl halide.

Sources & evidence

ORD record
ord-6c483e0201404b9c8ceb98953317125d
Source dataset
uspto-grants-2012_05
Patent number
US08168654B2

Reaction notes

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