Phenacyl bromide → (R)-3-((R)-2-(tert-butoxycarbonylamino)-2-phenylacetoxy)-1-(2-oxo-2-phenylethyl)-1-azoniabicyclo[2.2.2]octane bromide

HRID 1619501Notes

Reaction equation

HRID 1619501 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]([O:15][C:16]([NH:18][C@H:19]([C:31]1[CH:36]=[CH:35][CH:34]=[CH:33][CH:32]=1)[C:20]([O:22][C@@H:23]1[CH:28]2[CH2:29][CH2:30][N:25]([CH2:26][CH2:27]2)[CH2:24]1)=[O:21])=[O:17])([CH3:14])([CH3:13])[CH3:12]>CCOC(C)=O>[Br-:1].[C:11]([O:15][C:16]([NH:18][C@H:19]([C:31]1[CH:36]=[CH:35][CH:34]=[CH:33][CH:32]=1)[C:20]([O:22][C@@H:23]1[CH:28]2[CH2:29][CH2:30][N+:25]([CH2:2][C:3](=[O:4])[C:5]3[CH:10]=[CH:9][CH:8]=[CH:7][CH:6]=3)([CH2:26][CH2:27]2)[CH2:24]1)=[O:21])=[O:17])([CH3:14])([CH3:12])[CH3:13]

Participants

4

Reactant 2

HCID 6259Phenacyl bromideHCID 67607970(R)-((R)-quinuclidin-3-yl) 2-(tert-butoxycarbonylamino)-2-phenylacetate

Product 1

HCID 86665812(R)-3-((R)-2-(tert-butoxycarbonylamino)-2-phenylacetoxy)-1-(2-oxo-2-phenylethyl)-1-azoniabicyclo[2.2.2]octane bromideYield 84%

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

2-Bromo-1-phenylethanone (27.6 mg, 0.14 mmol) was added to a solution of (R)—((R)-quinuclidin-3-yl) 2-(tert-butoxycarbonylamino)-2-phenylacetate (Diasteroisomer 1 of C1) (50 mg, 0.14 mmol) in EtOAc (3 ml). The reaction was stirred at RT overnight. The precipitate was collected by suction filtration and washed with Et2O to obtain (R)-3-((R)-2-(tert-butoxycarbonylamino)-2-phenylacetoxy)-1-(2-oxo-2-phenylethyl)-1-azoniabicyclo[2.2.2]octane bromide (65 mg; 84% yield).

Workup

  1. filtrationThe precipitate was collected by suction filtration
  2. washwashed with Et2O

Sources & evidence

ORD record
ord-7bf88ee2fccf42c0ae27bf6274699727
Source dataset
uspto-grants-2014_07
Patent number
US08772314B2

Reaction notes

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