Phenacyl bromide → (3R)-1-(2-oxo-2-phenylethyl)-3-(2-phenyl-2-(piperidin-1-yl)acetoxy)-1-azoniabicyclo[2.2.2]octane bromide

HRID 404615Notes

Reaction equation

HRID 404615 reaction equation
[Br:1][CH2:2][C:3]([C:5]1[CH:10]=[CH:9][CH:8]=[CH:7][CH:6]=1)=[O:4].[C:11]1([CH:17]([N:29]2[CH2:34][CH2:33][CH2:32][CH2:31][CH2:30]2)[C:18]([O:20][C@@H:21]2[CH:26]3[CH2:27][CH2:28][N:23]([CH2:24][CH2:25]3)[CH2:22]2)=[O:19])[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1>CCOC(C)=O>[Br-:1].[O:4]=[C:3]([C:5]1[CH:10]=[CH:9][CH:8]=[CH:7][CH:6]=1)[CH2:2][N+:23]12[CH2:24][CH2:25][CH:26]([CH2:27][CH2:28]1)[C@@H:21]([O:20][C:18](=[O:19])[CH:17]([C:11]1[CH:12]=[CH:13][CH:14]=[CH:15][CH:16]=1)[N:29]1[CH2:30][CH2:31][CH2:32][CH2:33][CH2:34]1)[CH2:22]2

Participants

4

Reactant 2

HCID 6259Phenacyl bromideHCID 71603247(R)-quinuclidin-3-yl 2-phenyl-2-(piperidin-1-yl)acetate

Product 1

HCID 86688873(3R)-1-(2-oxo-2-phenylethyl)-3-(2-phenyl-2-(piperidin-1-yl)acetoxy)-1-azoniabicyclo[2.2.2]octane bromideYield 79,003.703%

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

2-Bromo-1-phenylethanone (91.0 mg, 0.46 mmol) was added to a solution of (R)-quinuclidin-3-yl 2-phenyl-2-(piperidin-1-yl)acetate (150 mg, 0.46 mmol) in EtOAc (10 ml). The mixture was stirred at room temperature for 3 hours. The precipitate was collected by suction filtration to obtain (3R)-1-(2-oxo-2-phenylethyl)-3-(2-phenyl-2-(piperidin-1-yl)acetoxy)-1-azoniabicyclo[2.2.2]octane bromide (191.7 g, 80% yield) as a white solid.

Workup

  1. filtrationThe precipitate was collected by suction filtration

Sources & evidence

ORD record
ord-954e965e736e4c39b6d41d89564d392b
Source dataset
uspto-grants-2014_06
Patent number
US08748613B2

Reaction notes

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