Phenacyl bromide → HCID 86665840, compound

HRID 1619531Notes

Reaction equation

HRID 1619531 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][C:34]([F:37])=[CH:33][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>[O:4]([CH:3]([CH3:2])[CH3:5])[CH:11]([CH3:13])[CH3:12].[Br-:1].[C:11]([O:15][C:16]([NH:18][CH:19]([C:31]1[CH:36]=[CH:35][C:34]([F:37])=[CH:33][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

6

Reactant 2

HCID 6259Phenacyl bromideHCID 67607323HCID 67607323, compound

Product 2

HCID 7914Diisopropyl EtherHCID 86665840HCID 86665840, compoundYield 99.8%

Reagents, catalysts & solvents 2

HCID 6342AcetonitrileSolventHCID 8857Ethyl AcetateSolvent

Procedure

2-Bromo-1-phenylethanone (34.7 mg, 0.17 mmol) is added to a solution of (R)-quinuclidin-3-yl 2-(tert-butoxycarbonylamino)-2-(4-fluorophenyl)-acetate (C50) (60.0 mg, 0.16 mmol) in EtOAc (2 ml) and acetonitrile (2 ml). The reaction was stirred at RT for 15 hours, and then the solvent was evaporated. The resulting residue was triturated with i-Pr2O/EtOAc (10/1) and then i-Pr2O to obtain (3R)-3-(2-(tert-butoxycarbonyl-amino)-2-(4-fluorophenyl)acetoxy)-1-(2-oxo-2-phenylethyl)-1-azoniabicyclo-[2.2.2]octane bromide (46.1 mg; 50% yield).

Workup

  1. customthe solvent was evaporated
  2. customThe resulting residue was triturated with i-Pr2O/EtOAc (10/1)

Sources & evidence

ORD record
ord-59d3acee70ee42c28a1b2a78dd3a68f0
Source dataset
uspto-grants-2014_07
Patent number
US08772314B2

Reaction notes

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