2-Chloroacetophenone → (R)-3-((bis(3-fluorophenyl)methoxy)carbonylamino)-1-(2-oxo-2-phenylethyl)-1-azoniabicyclo[2.2.2]octane chloride

HRID 1910487Notes

Reaction equation

HRID 1910487 reaction equation
[Cl:1][CH2:2][C:3]([C:5]1[CH:10]=[CH:9][CH:8]=[CH:7][CH:6]=1)=[O:4].[N:11]12[CH2:18][CH2:17][CH:14]([CH2:15][CH2:16]1)[C@@H:13]([NH:19][C:20](=[O:37])[O:21][CH:22]([C:30]1[CH:35]=[CH:34][CH:33]=[C:32]([F:36])[CH:31]=1)[C:23]1[CH:28]=[CH:27][CH:26]=[C:25]([F:29])[CH:24]=1)[CH2:12]2>C(OCC)(=O)C>[Cl-:1].[F:36][C:32]1[CH:31]=[C:30]([CH:22]([C:23]2[CH:28]=[CH:27][CH:26]=[C:25]([F:29])[CH:24]=2)[O:21][C:20]([NH:19][C@@H:13]2[CH:14]3[CH2:17][CH2:18][N+:11]([CH2:2][C:3](=[O:4])[C:5]4[CH:10]=[CH:9][CH:8]=[CH:7][CH:6]=4)([CH2:16][CH2:15]3)[CH2:12]2)=[O:37])[CH:35]=[CH:34][CH:33]=1

Participants

4

Reactant 2

HCID 107572-ChloroacetophenoneHCID 66575633(R)-bis(3-fluorophenyl)methyl quinuclidin-3-ylcarbamate

Product 1

HCID 86672924(R)-3-((bis(3-fluorophenyl)methoxy)carbonylamino)-1-(2-oxo-2-phenylethyl)-1-azoniabicyclo[2.2.2]octane chlorideYield 54.3%

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

2-Chloro-1-phenylethanone (20.8 mg, 0.13 mmol) was added to a solution of (R)-bis(3-fluorophenyl)methyl quinuclidin-3-ylcarbamate (50 mg, 0.13 mmol, prepared as in example 1) in ethyl acetate (2 ml). The reaction was stirred at room temperature overnight, then the solvent was evaporated under vacuum. The residue was treated with Et2O (4 ml) and sonicated to obtain a solid, which was collected by suction filtration and purified by flash chromatography (DCM/MeOH=95/5), to obtain (R)-3-((bis(3-fluorophenyl)methoxy)carbonylamino)-1-(2-oxo-2-phenylethyl)-1-azoniabicyclo[2.2.2]octane chloride (37.2 mg).

Workup

  1. customthe solvent was evaporated under vacuum
  2. additionThe residue was treated with Et2O (4 ml)
  3. customsonicated
  4. customto obtain a solid, which
  5. filtrationwas collected by suction filtration
  6. custompurified by flash chromatography (DCM/MeOH=95/5)

Sources & evidence

ORD record
ord-47515ba988a44912aef85253ac364f83
Source dataset
uspto-grants-2013_12
Patent number
US08604015B2

Reaction notes

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