Diethyl Ether → HCID 86665816, compound

HRID 1619504Notes

Reaction equation

HRID 1619504 reaction equation
[Br:1][CH2:2][C:3]([C:5]1[CH:9]=[CH:8][S:7][CH:6]=1)=[O:4].[C:10]([O:14][C:15]([NH:17][CH:18]([C:30]1[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=1)[C:19]([O:21][C@@H:22]1[CH:27]2[CH2:28][CH2:29][N:24]([CH2:25][CH2:26]2)[CH2:23]1)=[O:20])=[O:16])([CH3:13])([CH3:12])[CH3:11].CCOCC>C(OCC)(=O)C>[Br-:1].[C:10]([O:14][C:15]([NH:17][CH:18]([C:30]1[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=1)[C:19]([O:21][C@@H:22]1[CH:27]2[CH2:28][CH2:29][N+:24]([CH2:2][C:3](=[O:4])[C:5]3[CH:9]=[CH:8][S:7][CH:6]=3)([CH2:25][CH2:26]2)[CH2:23]1)=[O:20])=[O:16])([CH3:13])([CH3:11])[CH3:12]

Participants

5

Reactant 3

HCID 3283Diethyl EtherHCID 27763792-Bromo-1-(thiophen-3-yl)ethan-1-oneHCID 67425060(R)-quinuclidin-3-yl 2-(tert-butoxycarbonylamino)-2-phenylacetate

Product 1

HCID 86665816HCID 86665816, compoundYield 51.7%

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

2-Bromo-1-(thiophen-3-yl)ethanone (39.8 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 ethyl acetate (2 ml). The reaction was stirred at RT overnight. Et2O (1 ml) was added, and the solid was collected by suction filtration. The compound was further purified by flash chromatography (DCM/MeOH=95/5) to obtain (3R)-3-(2-(tert-butoxycarbonylamino)-2-phenylacetoxy)-1-(2-oxo-2-(thiophen-3-yl)ethyl)-1-azoniabicyclo[2.2.2]octane bromide (55.6 mg; 51% yield).

Workup

  1. filtrationthe solid was collected by suction filtration
  2. customThe compound was further purified by flash chromatography (DCM/MeOH=95/5)

Sources & evidence

ORD record
ord-1c631c3c44aa450bb2a962441bd8b83d
Source dataset
uspto-grants-2014_07
Patent number
US08772314B2

Reaction notes

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