2-(Chloroacetyl)thiophene → HCID 86672932, compound

HRID 1910495Notes

Reaction equation

HRID 1910495 reaction equation
[N:1]12[CH2:8][CH2:7][CH:4]([CH2:5][CH2:6]1)[C@@H:3]([NH:9][C:10](=[O:27])[O:11][CH:12]([C:20]1[CH:25]=[CH:24][CH:23]=[CH:22][C:21]=1[Cl:26])[C:13]1[CH:18]=[CH:17][C:16]([Cl:19])=[CH:15][CH:14]=1)[CH2:2]2.Cl[CH2:29][C:30]([C:32]1[S:33][CH:34]=[CH:35][CH:36]=1)=[O:31]>C(OCC)(=O)C>[Cl-:19].[Cl:26][C:21]1[CH:22]=[CH:23][CH:24]=[CH:25][C:20]=1[CH:12]([C:13]1[CH:14]=[CH:15][C:16]([Cl:19])=[CH:17][CH:18]=1)[O:11][C:10]([NH:9][C@@H:3]1[CH:4]2[CH2:7][CH2:8][N+:1]([CH2:29][C:30](=[O:31])[C:32]3[S:33][CH:34]=[CH:35][CH:36]=3)([CH2:6][CH2:5]2)[CH2:2]1)=[O:27]

Participants

4

Reactant 2

HCID 27579252-(Chloroacetyl)thiopheneHCID 70938644HCID 70938644, compound

Product 1

HCID 86672932HCID 86672932, compoundYield 69.1%

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

To a solution of (2-chlorophenyl)(4-chlorophenyl)methyl(R)-quinuclidin-3-ylcarbamate (95.0 mg, 0.23 mmol) in ethyl acetate (3 ml), 2-chloro-1-(thiophen-2-yl)ethanone (37.6 mg, 0.23 mmol) was added, and the mixture was stirred at room temperature overnight. The solvent was removed under vacuum, and the residue was taken up in diethyl ether and filtered. The product was purified by flash chromatography (DCM/MeOH=95/5) to obtain (3R)-3-(((2-chlorophenyl)(4-chlorophenyl)methoxy)carbonylamino)-1-(2-oxo-2-(thiophen-2-yl)ethyl)-1-azoniabicyclo[2.2.2]octane chloride (45.0 mg, mixture of diastereoisomers).

Workup

  1. customThe solvent was removed under vacuum
  2. filtrationfiltered
  3. customThe product was purified by flash chromatography (DCM/MeOH=95/5)

Sources & evidence

ORD record
ord-5e7f92806bc941c7a4cbd88cc314426e
Source dataset
uspto-grants-2013_12
Patent number
US08604015B2

Reaction notes

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