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 1255079Notes

Reaction equation

HRID 1255079 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-9f3c38d08e0a4060a9c3b0b281f0a48d
Source dataset
uspto-grants-2013_06
Patent number
US08455646B2

Reaction notes

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