Phenacyl bromide → HCID 86665844, compound

HRID 1619535Notes

Reaction equation

HRID 1619535 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]=[CH:33][C:32]=1[F:37])[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]=[CH:33][C:32]=1[F:37])[C:20]([O:22][C@@H:23]1[CH:28]2[CH2:29][CH2:30][N+:25]([CH2:2][C:3](=[O:4])[C:5]3[CH:10]=[CH:9][CH:8]=[CH:7][CH:6]=3)([CH2:26][CH2:27]2)[CH2:24]1)=[O:21])=[O:17])([CH3:14])([CH3:12])[CH3:13]

Participants

5

Reactant 2

HCID 6259Phenacyl bromideHCID 67607470HCID 67607470, compound

Product 1

HCID 86665844HCID 86665844, compoundYield 63.3%

Reagents, catalysts & solvents 2

HCID 6342AcetonitrileSolventHCID 8857Ethyl AcetateSolvent

Procedure

2-Bromo-1-phenylethanone (57.9 mg, 0.29 mmol) was added to a solution of (R)-quinuclidin-3-yl 2-(tert-butoxycarbonylamino)-2-(2-fluorophenyl)acetate (C56) (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-(2-fluorophenyl)acetoxy)-1-(2-oxo-2-phenylethyl)-1-azoniabicyclo[2.2.2]octane bromide (95.1 mg; 62% yield).

Workup

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

Sources & evidence

ORD record
ord-c084e6bc8e25404c953a59a96d836f45
Source dataset
uspto-grants-2014_07
Patent number
US08772314B2

Reaction notes

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