Phenacyl bromide → HCID 86665832, compound

HRID 1619521Notes

Reaction equation

HRID 1619521 reaction equation
[CH3:1][O:2][CH2:3][CH2:4][O:5][C:6]([NH:8][CH:9]([C:21]1[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=1)[C:10]([O:12][C@@H:13]1[CH:18]2[CH2:19][CH2:20][N:15]([CH2:16][CH2:17]2)[CH2:14]1)=[O:11])=[O:7].[Br:27][CH2:28][C:29]([C:31]1[CH:36]=[CH:35][CH:34]=[CH:33][CH:32]=1)=[O:30]>CCOC(C)=O.C(#N)C>[Br-:27].[CH3:1][O:2][CH2:3][CH2:4][O:5][C:6]([NH:8][CH:9]([C:21]1[CH:22]=[CH:23][CH:24]=[CH:25][CH:26]=1)[C:10]([O:12][C@@H:13]1[CH:18]2[CH2:17][CH2:16][N+:15]([CH2:28][C:29](=[O:30])[C:31]3[CH:36]=[CH:35][CH:34]=[CH:33][CH:32]=3)([CH2:20][CH2:19]2)[CH2:14]1)=[O:11])=[O:7]

Participants

5

Reactant 2

HCID 6259Phenacyl bromideHCID 67607069HCID 67607069, compound

Product 1

HCID 86665832HCID 86665832, compoundYield 54.6%

Reagents, catalysts & solvents 2

HCID 6342AcetonitrileSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a solution of (R)-quinuclidin-3-yl 2-((2-methoxyethoxy)-carbonylamino)-2-phenylacetate (C36) (73.0 mg, 0.20 mmol) in EtOAc (3 ml) and acetonitrile (1 ml), was added 2-bromo-1-phenylethanone (44.1 mg, 0.22 mmol). The reaction was stirred at RT for 15 hours, and then the solvent was evaporated, and the resulting crude was purified by flash chromatography (DCM/MeOH=95/5 to 93/7). The product was triturated with i-Pr2O to obtain (3R)-3-(2-((2-methoxyethoxy)carbonylamino)-2-phenylacetoxy)-1-(2-oxo-2-phenylethyl)-1-azoniabicyclo[2.2.2]octane bromide (61.3 mg; 54% yield).

Workup

  1. customthe solvent was evaporated
  2. customthe resulting crude was purified by flash chromatography (DCM/MeOH=95/5 to 93/7)
  3. customThe product was triturated with i-Pr2O

Sources & evidence

ORD record
ord-24a7372264ff4f718c0fe0f868d020dd
Source dataset
uspto-grants-2014_07
Patent number
US08772314B2

Reaction notes

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