2-Chloroacetophenone → (3R)-1-(2-oxo-2-phenylethyl)-3-(2-(2-oxopyrrolidin-1-yl)-2-phenylacetoxy)-1-azoniabicyclo[2.2.2]octane chloride

HRID 404667Notes

Reaction equation

HRID 404667 reaction equation
[Cl:1][CH2:2][C:3]([C:5]1[CH:10]=[CH:9][CH:8]=[CH:7][CH:6]=1)=[O:4].[O:11]=[C:12]1[CH2:16][CH2:15][CH2:14][N:13]1[CH:17]([C:29]1[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=1)[C:18]([O:20][C@@H:21]1[CH:26]2[CH2:27][CH2:28][N:23]([CH2:24][CH2:25]2)[CH2:22]1)=[O:19]>CCOC(C)=O.C(#N)C>[Cl-:1].[O:4]=[C:3]([C:5]1[CH:10]=[CH:9][CH:8]=[CH:7][CH:6]=1)[CH2:2][N+:23]12[CH2:24][CH2:25][CH:26]([CH2:27][CH2:28]1)[C@@H:21]([O:20][C:18](=[O:19])[CH:17]([N:13]1[CH2:14][CH2:15][CH2:16][C:12]1=[O:11])[C:29]1[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=1)[CH2:22]2

Participants

5

Reactant 2

HCID 107572-ChloroacetophenoneHCID 86688927(R)-quinuclidin-3-yl 2-(2-oxopyrrolidin-1-yl)-2-phenylacetate

Product 1

HCID 86688928(3R)-1-(2-oxo-2-phenylethyl)-3-(2-(2-oxopyrrolidin-1-yl)-2-phenylacetoxy)-1-azoniabicyclo[2.2.2]octane chlorideYield 67.9%

Reagents, catalysts & solvents 2

HCID 6342AcetonitrileSolventHCID 8857Ethyl AcetateSolvent

Procedure

2-Chloro-1-phenylethanone (62.1 mg, 0.40 mmol) was added to a solution of (R)-quinuclidin-3-yl 2-(2-oxopyrrolidin-1-yl)-2-phenylacetate (120 mg, 0.36 mmol) in EtOAc (2.4 ml) and acetonitrile (1.2 ml). The pale yellow solution was stirred at room temperature for three days. The solvent was evaporated and the crude was purified by flash chromatography (DCM/MeOH=9/1) to collect the title compound (118 mg, 66.9% yield) as an off-white spongy solid.

Workup

  1. customThe solvent was evaporated
  2. customthe crude was purified by flash chromatography (DCM/MeOH=9/1)

Sources & evidence

ORD record
ord-6a8866aedb5848b7be26458da4bbc8f4
Source dataset
uspto-grants-2014_06
Patent number
US08748613B2

Reaction notes

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