Phenacyl bromide → (R)-3-[2-(3-fluoro-4-methyl-phenylamino)-2-phenyl-acetoxy]-1-(2-oxo-2-phenyl-ethyl)-1-azonia-bicyclo[2.2.2]octane bromide

HRID 77034Notes

Reaction equation

HRID 77034 reaction equation
[F:1][C:2]1[CH:3]=[C:4]([NH:9][CH:10]([C:22]2[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=2)[C:11]([O:13][C@@H:14]2[CH:19]3[CH2:20][CH2:21][N:16]([CH2:17][CH2:18]3)[CH2:15]2)=[O:12])[CH:5]=[CH:6][C:7]=1[CH3:8].[Br:28][CH2:29][C:30]([C:32]1[CH:37]=[CH:36][CH:35]=[CH:34][CH:33]=1)=[O:31]>C(#N)C>[Br-:28].[F:1][C:2]1[CH:3]=[C:4]([NH:9][CH:10]([C:22]2[CH:23]=[CH:24][CH:25]=[CH:26][CH:27]=2)[C:11]([O:13][C@@H:14]2[CH:19]3[CH2:20][CH2:21][N+:16]([CH2:29][C:30](=[O:31])[C:32]4[CH:37]=[CH:36][CH:35]=[CH:34][CH:33]=4)([CH2:17][CH2:18]3)[CH2:15]2)=[O:12])[CH:5]=[CH:6][C:7]=1[CH3:8]

Participants

4

Reactant 2

HCID 6259Phenacyl bromideHCID 46840706HCID 46840706, compound

Product 1

HCID 86643221(R)-3-[2-(3-fluoro-4-methyl-phenylamino)-2-phenyl-acetoxy]-1-(2-oxo-2-phenyl-ethyl)-1-azonia-bicyclo[2.2.2]octane bromideYield 23.2%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

(R)-Quinuclidin-3-yl 2-(3-fluoro-4-methylphenylamino)-2-phenylacetate (C97) (80 mg, 0.22 mmol) and 2-bromo-1-phenylethanone (45.4 mg, 0.23 mmol) are dissolved in acetonitrile (3 mL) and stirred at RT overnight (Conversion complete by UPLC/MS). Acetonitrile is evaporated and the residue is purified by flash chromatography (DCM/MeOH=97/3) affording thetitle compound as a white solid (29 mg, 23% yield, bromide salt, mixture of diastereoisomers).

Workup

  1. customAcetonitrile is evaporated
  2. customthe residue is purified by flash chromatography (DCM/MeOH=97/3)

Sources & evidence

ORD record
ord-6daa51eda9f24dbba42faaaeb1696e14
Source dataset
uspto-grants-2014_09
Patent number
US08835682B2

Reaction notes

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