2-Chloroacetophenone → (3R)-3-(2-benzamido-2-phenylacetoxy)-1-(2-oxo-2-phenylethyl)-1-azoniabicyclo[2.2.2]octane chloride

HRID 1619561Notes

Reaction equation

HRID 1619561 reaction equation
[C:1]([NH:9][CH:10]([C:22]1[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=1)[C:11]([O:13][C@@H:14]1[CH:19]2[CH2:20][CH2:21][N:16]([CH2:17][CH2:18]2)[CH2:15]1)=[O:12])(=[O:8])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[Cl:28][CH2:29][C:30]([C:32]1[CH:37]=[CH:36][CH:35]=[CH:34][CH:33]=1)=[O:31]>CCOC(C)=O.C(#N)C>[Cl-:28].[C:1]([NH:9][CH:10]([C:22]1[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=1)[C:11]([O:13][C@@H:14]1[CH:19]2[CH2:18][CH2:17][N+:16]([CH2:29][C:30](=[O:31])[C:32]3[CH:37]=[CH:36][CH:35]=[CH:34][CH:33]=3)([CH2:21][CH2:20]2)[CH2:15]1)=[O:12])(=[O:8])[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

5

Reactant 2

HCID 107572-ChloroacetophenoneHCID 67605943(R)-quinuclidin-3-yl 2-benzamido-2-phenylacetate

Product 1

HCID 86665854(3R)-3-(2-benzamido-2-phenylacetoxy)-1-(2-oxo-2-phenylethyl)-1-azoniabicyclo[2.2.2]octane chlorideYield 73%

Reagents, catalysts & solvents 2

HCID 6342AcetonitrileSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a solution of (R)-quinuclidin-3-yl 2-benzamido-2-phenylacetate (C85) (70 mg, 0.19 mmol) in EtOAc (1 ml) and acetonitrile (1 ml), was added 2-chloro-1-phenylethanone (32.7 mg, 0.21 mmol). The reaction was stirred at RT for 24 hours, and then the solvents were evaporated and the residue was triturated with EtOAc (8 ml) to obtain (3R)-3-(2-benzamido-2-phenylacetoxy)-1-(2-oxo-2-phenylethyl)-1-azoniabicyclo[2.2.2]octane chloride (72 mg; 72% yield).

Workup

  1. customthe solvents were evaporated
  2. customthe residue was triturated with EtOAc (8 ml)

Sources & evidence

ORD record
ord-2e2c1ab15ac14a9293283208b1bec847
Source dataset
uspto-grants-2014_07
Patent number
US08772314B2

Reaction notes

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