Diethyl Ether → HCID 86665814, compound

HRID 1619503Notes

Reaction equation

HRID 1619503 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[CH:36]=[CH:35][CH:34]=[CH:33][CH:32]=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].CCOCC>CCOC(C)=O>[Cl-:1].[C:11]([O:15][C:16]([NH:18][CH:19]([C:31]1[CH:36]=[CH:35][CH:34]=[CH:33][CH:32]=1)[C:20]([O:22][C@@H:23]1[CH:28]2[CH2:29][CH2:30][N+:25]([CH2:2][C:3](=[O:4])[C:5]3[CH:10]=[CH:9][CH:8]=[CH:7][CH:6]=3)([CH2:26][CH2:27]2)[CH2:24]1)=[O:21])=[O:17])([CH3:14])([CH3:12])[CH3:13]

Participants

5

Reactant 3

HCID 3283Diethyl EtherHCID 107572-ChloroacetophenoneHCID 67425060(R)-quinuclidin-3-yl 2-(tert-butoxycarbonylamino)-2-phenylacetate

Product 1

HCID 86665814HCID 86665814, compoundYield 55.8%

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

2-Chloro-1-phenylethanone (30.0 mg, 0.19 mmol) was added to a solution of (R)-quinuclidin-3-yl 2-(tert-butoxycarbonylamino)-2-phenylacetate (C1) (70.0 mg, 0.19 mmol) in EtOAc (2 ml). The reaction was stirred at RT for 24 hours. Then Et2O (1 ml) was added, and the reaction was sonicated. The solid was collected by suction filtration to obtain (3R)-3-(2-(tert-butoxycarbonylamino)-2-phenylacetoxy)-1-(2-oxo-2-phenylethyl)-1-azoniabicyclo[2.2.2]octane chloride (54.6 mg; 55% yield).

Workup

  1. customthe reaction was sonicated
  2. filtrationThe solid was collected by suction filtration

Sources & evidence

ORD record
ord-65728ab6b8df48a7bbff2c9b4bde95fd
Source dataset
uspto-grants-2014_07
Patent number
US08772314B2

Reaction notes

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