2-Chloroacetophenone → (3R)-1-(2-oxo-2-phenylethyl)-3-(2-phenyl-2-(phenylsulfonamido)acetoxy)-1-azoniabicyclo[2.2.2]octane chloride

HRID 1619544Notes

Reaction equation

HRID 1619544 reaction equation
[C:1]1([CH:7]([NH:19][S:20]([C:23]2[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=2)(=[O:22])=[O:21])[C:8]([O:10][C@@H:11]2[CH:16]3[CH2:17][CH2:18][N:13]([CH2:14][CH2:15]3)[CH2:12]2)=[O:9])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[Cl:29][CH2:30][C:31]([C:33]1[CH:38]=[CH:37][CH:36]=[CH:35][CH:34]=1)=[O:32]>CCOC(C)=O.C(#N)C>[Cl-:29].[O:32]=[C:31]([C:33]1[CH:38]=[CH:37][CH:36]=[CH:35][CH:34]=1)[CH2:30][N+:13]12[CH2:14][CH2:15][CH:16]([CH2:17][CH2:18]1)[C@@H:11]([O:10][C:8](=[O:9])[CH:7]([C:1]1[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1)[NH:19][S:20]([C:23]1[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=1)(=[O:22])=[O:21])[CH2:12]2

Participants

5

Reactant 2

HCID 107572-ChloroacetophenoneHCID 67607322(R)-quinuclidin-3-yl 2-phenyl-2-(phenylsulfonamido)acetate

Product 1

HCID 86665846(3R)-1-(2-oxo-2-phenylethyl)-3-(2-phenyl-2-(phenylsulfonamido)acetoxy)-1-azoniabicyclo[2.2.2]octane chlorideYield 74.3%

Reagents, catalysts & solvents 2

HCID 6342AcetonitrileSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a solution of (R)-quinuclidin-3-yl 2-phenyl-2-(phenylsulfonamido)acetate (C64) (96 mg, 0.24 mmol) in EtOAc (1.6 ml) and acetonitrile (0.8 ml), was added 2-chloro-1-phenylethanone (40.8 mg, 0.26 mmol). The solution was stirred at RT overnight. The solution was concentrated under vacuum and the crude was purified by flash chromatography (DCM/MeOH=95/5 to 9/1) to obtain (3R)-1-(2-oxo-2-phenylethyl)-3-(2-phenyl-2-(phenylsulfonamido)acetoxy)-1-azoniabicyclo[2.2.2]octane chloride (99 mg; 74% yield).

Workup

  1. concentrationThe solution was concentrated under vacuum
  2. customthe crude was purified by flash chromatography (DCM/MeOH=95/5 to 9/1)

Sources & evidence

ORD record
ord-8c807519b637411ea4f1cc40f3b1ce60
Source dataset
uspto-grants-2014_07
Patent number
US08772314B2

Reaction notes

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