2-Bromo-2'-methylacetophenone → HCID 86660306, compound

HRID 453696Notes

Reaction equation

HRID 453696 reaction equation
[C:1]1([C@@H:7]([NH:19][C:20]2[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=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.[Br:26][CH2:27][C:28]([C:30]1[CH:35]=[CH:34][CH:33]=[CH:32][C:31]=1[CH3:36])=[O:29]>CCOC(C)=O>[Br-:26].[O:29]=[C:28]([C:30]1[CH:35]=[CH:34][CH:33]=[CH:32][C:31]=1[CH3:36])[CH2:27][N+:13]12[CH2:14][CH2:15][CH:16]([CH2:17][CH2:18]1)[C@@H:11]([O:10][C:8](=[O:9])[C@@H:7]([C:1]1[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=1)[NH:19][C:20]1[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1)[CH2:12]2

Participants

4

Reactant 2

HCID 124306762-Bromo-2'-methylacetophenoneHCID 46840261(R)-((R)-quinuclidin-3-yl) 2-phenyl-2-(phenylamino)acetate

Product 1

HCID 86660306HCID 86660306, compoundYield 86.4%

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

To a solution of (R)—((R)-quinuclidin-3-yl) 2-phenyl-2-(phenylamino)acetate (diastereomer 1 of I2) (55 mg, 0.16 mmol) in EtOAc (5 ml), was added 2-bromo-1-o-tolylethanone (41.8 mg, 0.20 mmol), and the reaction was stirred at room temperature for 15 hours. The precipitate was collected by suction filtration to obtain (R)-1-(2-oxo-2-o-tolylethyl)-3-((R)-2-phenyl-2-(phenylamino)acetoxy)-1-azoniabicyclo[2.2.2]octane bromide (76.0 mg, 85% yield).

Workup

  1. filtrationThe precipitate was collected by suction filtration

Sources & evidence

ORD record
ord-255f54f99df644f0a0e48ddb3284e0cd
Source dataset
uspto-grants-2013_07
Patent number
US08492548B2

Reaction notes

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