2-Butene, 1-bromo-3-methyl- → (3R)-3-(2-(3-(ethoxycarbonyl)phenylamino)-2-(6-methoxypyridin-3-yl)acetoxy)-1-(3-methylbut-2-enyl)-1-azoniabicyclo[2.2.2]octane bromide

HRID 469504Notes

Reaction equation

HRID 469504 reaction equation
[Br:1][CH2:2][CH:3]=[C:4]([CH3:6])[CH3:5].[CH3:7][O:8][C:9]1[N:14]=[CH:13][C:12]([CH:15]([NH:27][C:28]2[CH:29]=[C:30]([CH:36]=[CH:37][CH:38]=2)[C:31]([O:33][CH2:34][CH3:35])=[O:32])[C:16](=[O:26])[O:17][C@@H:18]2[CH:23]3[CH2:24][CH2:25][N:20]([CH2:21][CH2:22]3)[CH2:19]2)=[CH:11][CH:10]=1>CCOC(C)=O>[Br-:1].[CH2:34]([O:33][C:31]([C:30]1[CH:29]=[C:28]([NH:27][CH:15]([C:12]2[CH:13]=[N:14][C:9]([O:8][CH3:7])=[CH:10][CH:11]=2)[C:16]([O:17][C@@H:18]2[CH:23]3[CH2:24][CH2:25][N+:20]([CH2:2][CH:3]=[C:4]([CH3:6])[CH3:5])([CH2:21][CH2:22]3)[CH2:19]2)=[O:26])[CH:38]=[CH:37][CH:36]=1)=[O:32])[CH3:35]

Participants

4

Reactant 2

HCID 700922-Butene, 1-bromo-3-methyl-HCID 58556990ethyl 3-(1-(6-methoxypyridin-3-yl)-2-oxo-2-((R)-quinuclidin-3-yloxy)ethylamino)benzoate

Product 1

HCID 67124898(3R)-3-(2-(3-(ethoxycarbonyl)phenylamino)-2-(6-methoxypyridin-3-yl)acetoxy)-1-(3-methylbut-2-enyl)-1-azoniabicyclo[2.2.2]octane bromideYield 86.5%

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

1-Bromo-3-methylbut-2-ene (16.9 mg, 0.11 mmol) was added to a solution of ethyl 3-(1-(6-methoxypyridin-3-yl)-2-oxo-2-((R)-quinuclidin-3-yloxy)ethylamino)benzoate (C65) (50 mg, 0.11 mmol) in EtOAc (2 ml). The reaction mixture was stirred at room temperature overnight. The solvent was evaporated, and the residue was triturated with Et2O, filtered and dried. The product was purified by flash-chromatography (DCM/MeOH=97/3 to 9/1) to obtain (3R)-3-(2-(3-(ethoxycarbonyl)phenylamino)-2-(6-methoxypyridin-3-yl)acetoxy)-1-(3-methylbut-2-enyl)-1-azoniabicyclo[2.2.2]octane bromide (56 mg, 84% yield).

Workup

  1. customThe solvent was evaporated
  2. customthe residue was triturated with Et2O
  3. filtrationfiltered
  4. customdried
  5. customThe product was purified by flash-chromatography (DCM/MeOH=97/3 to 9/1)

Sources & evidence

ORD record
ord-7f5d8f9f91ea4544ad1011ac3d5f8a6e
Source dataset
uspto-grants-2014_01
Patent number
US08629160B2

Reaction notes

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