Diethyl Ether → (R)-3-((bis(3-fluorophenyl)methoxy)-carbonylamino)-1-(2-oxo-2-(pyridin-2-yl)ethyl)-1-azoniabicyclo[2.2.2]octane bromide

HRID 1910486Notes

Reaction equation

HRID 1910486 reaction equation
Br.[Br:2][CH2:3][C:4]([C:6]1[CH:11]=[CH:10][CH:9]=[CH:8][N:7]=1)=[O:5].[N:12]12[CH2:19][CH2:18][CH:15]([CH2:16][CH2:17]1)[C@@H:14]([NH:20][C:21](=[O:38])[O:22][CH:23]([C:31]1[CH:36]=[CH:35][CH:34]=[C:33]([F:37])[CH:32]=1)[C:24]1[CH:29]=[CH:28][CH:27]=[C:26]([F:30])[CH:25]=1)[CH2:13]2.CCOCC>C(OCC)(=O)C>[Br-:2].[F:37][C:33]1[CH:32]=[C:31]([CH:23]([C:24]2[CH:29]=[CH:28][CH:27]=[C:26]([F:30])[CH:25]=2)[O:22][C:21]([NH:20][C@@H:14]2[CH:15]3[CH2:16][CH2:17][N+:12]([CH2:3][C:4](=[O:5])[C:6]4[CH:11]=[CH:10][CH:9]=[CH:8][N:7]=4)([CH2:19][CH2:18]3)[CH2:13]2)=[O:38])[CH:36]=[CH:35][CH:34]=1

Participants

5

Reactant 3

HCID 3283Diethyl EtherHCID 27762312-Bromo-1-(2-pyridinyl)-1-ethanone hydrobromideHCID 66575633(R)-bis(3-fluorophenyl)methyl quinuclidin-3-ylcarbamate

Product 1

HCID 86672922(R)-3-((bis(3-fluorophenyl)methoxy)-carbonylamino)-1-(2-oxo-2-(pyridin-2-yl)ethyl)-1-azoniabicyclo[2.2.2]octane bromideYield 20.6%

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

2-Bromo-1-(pyridin-2-yl)ethanone hydrobromide (39.2 mg, 0.14 mmol) was added to a solution of (R)-bis(3-fluorophenyl)methyl quinuclidin-3-ylcarbamate (52 mg, 0.14 mmol, prepared as in example 1) in ethyl acetate (2 ml). The reaction was stirred at room temperature for 16 hours, then Et2O (1 mL) was added, and the precipitate was collected by suction filtration and dried under vacuum at 40° C. overnight. The product was further purified by preparative HPLC to obtain (R)-3-((bis(3-fluorophenyl)methoxy)-carbonylamino)-1-(2-oxo-2-(pyridin-2-yl)ethyl)-1-azoniabicyclo[2.2.2]octane bromide (16.5 mg).

Workup

  1. filtrationthe precipitate was collected by suction filtration
  2. customdried under vacuum at 40° C. overnight
  3. customThe product was further purified by preparative HPLC

Sources & evidence

ORD record
ord-409669436e4f45d9b5df04b79652ab82
Source dataset
uspto-grants-2013_12
Patent number
US08604015B2

Reaction notes

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