2-Chloroacetophenone → HCID 86665856, compound

HRID 1619572Notes

Reaction equation

HRID 1619572 reaction equation
[Cl: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[S:32][CH:33]=[CH:34][CH:35]=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>[Cl-:1].[C:11]([O:15][C:16]([NH:18][CH:19]([C:31]1[S:32][CH:33]=[CH:34][CH:35]=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

4

Reactant 2

HCID 107572-ChloroacetophenoneHCID 67605739HCID 67605739, compound

Product 1

HCID 86665856HCID 86665856, compoundYield 48.3%

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

2-Chloro-1-phenylethanone (43.0 mg, 0.28 mmol) was added to a solution of (R)-quinuclidin-3-yl 2-(tert-butoxycarbonylamino)-2-(thiophen-2-yl)acetate (102 mg, 0.28 mmol) in EtOAc (3 ml). The reaction was stirred at RT for 20 hours. The solvent was evaporated, and the crude was triturated with Et2O (2 ml) and dried under vacuum to obtain (3R)-3-(2-(tert-butoxycarbonylamino)-2-(thiophen-2-yl)acetoxy)-1-(2-oxo-2-phenylethyl)-1-azoniabicyclo[2.2.2]octane chloride (70 mg, 48.3% yield).

Workup

  1. customThe solvent was evaporated
  2. customthe crude was triturated with Et2O (2 ml)
  3. customdried under vacuum

Sources & evidence

ORD record
ord-23f52a1246f44a56b89b6c8f2871fd00
Source dataset
uspto-grants-2014_07
Patent number
US08772314B2

Reaction notes

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