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

HRID 1619519Notes

Reaction equation

HRID 1619519 reaction equation
[CH2:1]([O:3][C:4]([NH:6][CH:7]([C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1)[C:8]([O:10][C@@H:11]1[CH:16]2[CH2:17][CH2:18][N:13]([CH2:14][CH2:15]2)[CH2:12]1)=[O:9])=[O:5])[CH3:2].[Br:25][CH2:26][C:27]([C:29]1[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=1)=[O:28]>CCOC(C)=O.C(#N)C>[Br-:25].[CH2:1]([O:3][C:4]([NH:6][CH:7]([C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1)[C:8]([O:10][C@@H:11]1[CH:16]2[CH2:15][CH2:14][N+:13]([CH2:26][C:27](=[O:28])[C:29]3[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=3)([CH2:18][CH2:17]2)[CH2:12]1)=[O:9])=[O:5])[CH3:2]

Participants

5

Reactant 2

HCID 6259Phenacyl bromideHCID 67605831(R)-quinuclidin-3-yl 2-(ethoxycarbonylamino)-2-phenylacetate

Product 1

HCID 86665830(3R)-3-(2-(ethoxycarbonylamino)-2-phenylacetoxy)-1-(2-oxo-2-phenylethyl)-1-azoniabicyclo[2.2.2]octane bromideYield 80%

Reagents, catalysts & solvents 2

HCID 6342AcetonitrileSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a solution of (R)-quinuclidin-3-yl 2-(ethoxycarbonylamino)-2-phenylacetate (C34) (60.0 mg, 0.18 mmol) in EtOAc (2 ml) and acetonitrile (0.5 ml), was added 2-bromo-1-phenylethanone (39.5 mg, 0.20 mmol). The reaction was stirred at RT for 15 hours, and the solvent was evaporated. The resulting solid was triturated in i-Pr2O/EtOAc (1/1) to obtain (3R)-3-(2-(ethoxycarbonylamino)-2-phenylacetoxy)-1-(2-oxo-2-phenylethyl)-1-azoniabicyclo[2.2.2]octane bromide (76 mg; 80% yield).

Workup

  1. customthe solvent was evaporated
  2. customThe resulting solid was triturated in i-Pr2O/EtOAc (1/1)

Sources & evidence

ORD record
ord-9408f031b8634723aa213d9fe020c494
Source dataset
uspto-grants-2014_07
Patent number
US08772314B2

Reaction notes

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