3-(2-Bromoacetyl)benzonitrile → (R)-1-(2-(3-cyanophenyl)-2-oxoethyl)-3-((R)-2-phenyl-2-(phenylamino)acetoxy)-1-azoniabicyclo[2.2.2]octane bromide

HRID 453686

Reaction equation

HRID 453686 reaction equation
[Br:1][CH2:2][C:3]([C:5]1[CH:6]=[C:7]([CH:10]=[CH:11][CH:12]=1)[C:8]#[N:9])=[O:4].[C:13]1([C@@H:19]([NH:31][C:32]2[CH:37]=[CH:36][CH:35]=[CH:34][CH:33]=2)[C:20]([O:22][C@@H:23]2[CH:28]3[CH2:29][CH2:30][N:25]([CH2:26][CH2:27]3)[CH2:24]2)=[O:21])[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1>CCOC(C)=O>[Br-:1].[C:8]([C:7]1[CH:6]=[C:5]([C:3](=[O:4])[CH2:2][N+:25]23[CH2:26][CH2:27][CH:28]([CH2:29][CH2:30]2)[C@@H:23]([O:22][C:20](=[O:21])[C@@H:19]([C:13]2[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=2)[NH:31][C:32]2[CH:37]=[CH:36][CH:35]=[CH:34][CH:33]=2)[CH2:24]3)[CH:12]=[CH:11][CH:10]=1)#[N:9]

Participants

4

Reactant 2

HCID 27358673-(2-Bromoacetyl)benzonitrileHCID 46840261(R)-((R)-quinuclidin-3-yl) 2-phenyl-2-(phenylamino)acetate

Product 1

HCID 86660300(R)-1-(2-(3-cyanophenyl)-2-oxoethyl)-3-((R)-2-phenyl-2-(phenylamino)acetoxy)-1-azoniabicyclo[2.2.2]octane bromideYield 61%

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

3-(2-Bromoacetyl)benzonitrile (40.0 mg, 0.18 mmol) was added to a solution of (R)—((R)-quinuclidin-3-yl) 2-phenyl-2-(phenylamino)acetate (diastereomer 1 of I2) (60 mg, 0.18 mmol) in EtOAc (2 ml). The reaction mixture was stirred at room temperature overnight (UPLC-MS: complete conversion). EtOAc was removed under vacuum, and the residue is triturated with Et2O. The solid was collected by suction filtration and dried at 40° C. for 48 hours to obtain the (R)-1-(2-(3-cyanophenyl)-2-oxoethyl)-3-((R)-2-phenyl-2-(phenylamino)acetoxy)-1-azoniabicyclo[2.2.2]octane bromide (61.1 mg, 61% yield).

Workup

  1. customEtOAc was removed under vacuum
  2. customthe residue is triturated with Et2O
  3. filtrationThe solid was collected by suction filtration
  4. customdried at 40° C. for 48 hours

Sources & evidence

ORD record
ord-19944274fdfb450c86b7b3ae2a8d921c
Source dataset
uspto-grants-2013_07
Patent number
US08492548B2

Linked notes

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