2-Chloroacetophenone → HCID 86688892, compound

HRID 404632Notes

Reaction equation

HRID 404632 reaction equation
[C:1]1([CH:7]([N:19]2[CH2:23][CH2:22][CH2:21][CH2:20]2)[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:24][CH2:25][C:26]([C:28]1[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=1)=[O:27]>C(OCC)(=O)C>[Cl-:24].[O:27]=[C:26]([C:28]1[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=1)[CH2:25][N+:13]12[CH2:18][CH2:17][CH:16]([CH2:15][CH2:14]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)[N:19]1[CH2:23][CH2:22][CH2:21][CH2:20]1)[CH2:12]2

Participants

4

Reactant 2

HCID 107572-ChloroacetophenoneHCID 86688891HCID 86688891, compound

Product 1

HCID 86688892HCID 86688892, compoundYield 58.6%

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

(R)-Quinuclidin-3-yl 2-phenyl-2-(pyrrolidin-1-yl)acetate (51 mg, 0.16 mmol) was dissolved in ethyl acetate (1.6 ml) and 2-chloro-1-phenylethanone (25.1 mg, 0.16 mmol) was added. The solution was stirred at room temperature for 3.5 days. The suspension was evaporated and the residue was purified by flash chromatography (DCM/MeOH=9/1 to 85/15) to obtain (3R)-1-(2-oxo-2-phenylethyl)-3-(2-phenyl-2-(pyrrolidin-1-yl)acetoxy)-1-azoniabicyclo[2.2.2]octane chloride (44 mg, 57.8% yield) as a yellow vitreous solid.

Workup

  1. customThe suspension was evaporated
  2. customthe residue was purified by flash chromatography (DCM/MeOH=9/1 to 85/15)

Sources & evidence

ORD record
ord-6a9fed73e3744d688b47a9db1ed630db
Source dataset
uspto-grants-2014_06
Patent number
US08748613B2

Reaction notes

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