Phenacyl bromide → HCID 86665842, compound

HRID 1619533Notes

Reaction equation

HRID 1619533 reaction equation
[Br:1][CH2:2][C:3]([C:5]1[CH:10]=[CH:9][CH:8]=[CH:7][CH:6]=1)=[O:4].[C:11]([O:15][C:16]([NH:18][CH:19]([C:31]1[CH:36]=[CH:35][CH:34]=[C:33]([F:37])[CH:32]=1)[C:20]([O:22][C@@H:23]1[CH:28]2[CH2:29][CH2:30][N:25]([CH2:26][CH2:27]2)[CH2:24]1)=[O:21])=[O:17])([CH3:14])([CH3:13])[CH3:12]>CCOC(C)=O.C(#N)C>[Br-:1].[C:11]([O:15][C:16]([NH:18][CH:19]([C:31]1[CH:36]=[CH:35][CH:34]=[C:33]([F:37])[CH:32]=1)[C:20]([O:22][C@@H:23]1[CH:28]2[CH2:27][CH2:26][N+:25]([CH2:2][C:3](=[O:4])[C:5]3[CH:10]=[CH:9][CH:8]=[CH:7][CH:6]=3)([CH2:30][CH2:29]2)[CH2:24]1)=[O:21])=[O:17])([CH3:14])([CH3:12])[CH3:13]

Participants

5

Reactant 2

HCID 6259Phenacyl bromideHCID 67608105HCID 67608105, compound

Product 1

HCID 86665842HCID 86665842, compoundYield 47.1%

Reagents, catalysts & solvents 2

HCID 6342AcetonitrileSolventHCID 8857Ethyl AcetateSolvent

Procedure

2-Bromo-1-phenylethanone (63.1 mg, 0.32 mmol) was added to a solution of (R)-quinuclidin-3-yl 2-(tert-butoxycarbonylamino)-2-(3-fluorophenyl)acetate (C53) (100 mg, 0.26 mmol) in EtOAc (3 ml) and acetonitrile (3 ml). The reaction was stirred at RT for 15 hours, and then the solvent was evaporated. The crude was purified by flash chromatography (DCM/MeOH=94/6) to obtain (3R)-3-(2-(tert-butoxycarbonylamino)-2-(3-fluorophenyl)acetoxy)-1-(2-oxo-2-phenylethyl)-1-azoniabicyclo[2.2.2]octane bromide (70.7 mg; 46% yield).

Workup

  1. customthe solvent was evaporated
  2. customThe crude was purified by flash chromatography (DCM/MeOH=94/6)

Sources & evidence

ORD record
ord-cfd56ffb7e0a48cc90640f589f88c2a2
Source dataset
uspto-grants-2014_07
Patent number
US08772314B2

Reaction notes

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