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

HRID 77046Notes

Reaction equation

HRID 77046 reaction equation
[F:1][C:2]1[CH:27]=[CH:26][C:5]([CH2:6][NH:7][CH:8]([C:20]2[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=2)[C:9]([O:11][C@@H:12]2[CH:17]3[CH2:18][CH2:19][N:14]([CH2:15][CH2:16]3)[CH2:13]2)=[O:10])=[CH:4][CH:3]=1.[Br:28][CH2:29][C:30]([C:32]1[CH:37]=[CH:36][CH:35]=[CH:34][CH:33]=1)=[O:31]>C(OCC)(=O)C>[Br-:28].[F:1][C:2]1[CH:27]=[CH:26][C:5]([CH2:6][NH:7][CH:8]([C:20]2[CH:21]=[CH:22][CH:23]=[CH:24][CH:25]=2)[C:9]([O:11][C@@H:12]2[CH:17]3[CH2:16][CH2:15][N+:14]([CH2:29][C:30](=[O:31])[C:32]4[CH:37]=[CH:36][CH:35]=[CH:34][CH:33]=4)([CH2:19][CH2:18]3)[CH2:13]2)=[O:10])=[CH:4][CH:3]=1

Participants

4

Reactant 2

HCID 6259Phenacyl bromideHCID 59401102(R)-Quinuclidin-3-yl 2-(4-fluorobenzylamino)-2-phenylacetate

Product 1

HCID 86643234(R)-3-[2-(4-fluoro-benzylamino)-2-phenyl-acetoxy]-1-(2-oxo-2-phenyl-ethyl)-1-azonia-bicyclo[2.2.2]octane bromideYield 37%

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

A mixture of (R)-quinuclidin-3-yl 2-(4-fluorobenzylamino)-2-phenylacetate (C78) (61 mg, 0.17 mmol) and 2-bromo-1-phenylethanone (33.0 mg, 0.17 mmol) in ethyl acetate (3 mL) is stirred at RT overnight. The solid is collected by suction filtration and washed with Et2O. The product is further purified by flash chromatography (DCM/MeOH=95/5 to 92/8) to obtain the title compound as a white solid (35 mg, 37% yield, bromide salt, mixture of diastereoisomers).

Workup

  1. filtrationThe solid is collected by suction filtration
  2. washwashed with Et2O
  3. customThe product is further purified by flash chromatography (DCM/MeOH=95/5 to 92/8)

Sources & evidence

ORD record
ord-56d458a923b34510b329def04b424531
Source dataset
uspto-grants-2014_09
Patent number
US08835682B2

Reaction notes

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