2-Bromo-1-(thiophen-3-yl)ethan-1-one → (R)-3-(2-benzylamino-2-phenyl-acetoxy)-1-(2-oxo-2-thiophen-3-yl-ethyl)-1-azonia-bicyclo[2.2.2]octane bromide

HRID 77042Notes

Reaction equation

HRID 77042 reaction equation
[CH2:1]([NH:8][CH:9]([C:21]1[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=1)[C:10]([O:12][C@@H:13]1[CH:18]2[CH2:19][CH2:20][N:15]([CH2:16][CH2:17]2)[CH2:14]1)=[O:11])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[Br:27][CH2:28][C:29]([C:31]1[CH:35]=[CH:34][S:33][CH:32]=1)=[O:30]>C(OCC)(=O)C.C(#N)C>[Br-:27].[CH2:1]([NH:8][CH:9]([C:21]1[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=1)[C:10]([O:12][C@@H:13]1[CH:18]2[CH2:17][CH2:16][N+:15]([CH2:28][C:29](=[O:30])[C:31]3[CH:35]=[CH:34][S:33][CH:32]=3)([CH2:20][CH2:19]2)[CH2:14]1)=[O:11])[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

5

Reactant 2

HCID 27763792-Bromo-1-(thiophen-3-yl)ethan-1-oneHCID 46840418(R)-quinuclidin-3-yl 2-(benzylamino)-2-phenylacetate

Product 1

HCID 86643229(R)-3-(2-benzylamino-2-phenyl-acetoxy)-1-(2-oxo-2-thiophen-3-yl-ethyl)-1-azonia-bicyclo[2.2.2]octane bromideYield 14.6%

Reagents, catalysts & solvents 2

HCID 6342AcetonitrileSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a solution of (R)-quinuclidin-3-yl 2-(benzylamino)-2-phenylacetate (C80) (116 mg, 0.33 mmol) in ethyl acetate (3.31 mL) and acetonitrile (3.31 mL), is added 2-bromo-1-(thiophen-3-yl)ethanone (66.5 mg, 0.32 mmol). The mixture is stirred at RT overnight. The insoluble precipitate is filtered on a buckner funnel and washed with acetonitrile. The clear solution is evaporated and purified by flash chromatography (DCM/EtOH=9/1) to obtain the title compound as a white solid (26 mg, 14% yield, bromide salt, mixture of diastereoisomers).

Workup

  1. filtrationThe insoluble precipitate is filtered on a buckner funnel
  2. washwashed with acetonitrile
  3. customThe clear solution is evaporated
  4. custompurified by flash chromatography (DCM/EtOH=9/1)

Sources & evidence

ORD record
ord-cb4efcc83d524a708d456d499b0fb4e7
Source dataset
uspto-grants-2014_09
Patent number
US08835682B2

Reaction notes

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