Bromomethyl 2-methoxyphenyl ketone → HCID 86665818, compound

HRID 1619506Notes

Reaction equation

HRID 1619506 reaction equation
[Br:1][CH2:2][C:3]([C:5]1[CH:10]=[CH:9][CH:8]=[CH:7][C:6]=1[O:11][CH3:12])=[O:4].[C:13]([O:17][C:18]([NH:20][CH:21]([C:33]1[CH:38]=[CH:37][CH:36]=[CH:35][CH:34]=1)[C:22]([O:24][C@@H:25]1[CH:30]2[CH2:31][CH2:32][N:27]([CH2:28][CH2:29]2)[CH2:26]1)=[O:23])=[O:19])([CH3:16])([CH3:15])[CH3:14]>C(#N)C>[Br-:1].[C:13]([O:17][C:18]([NH:20][CH:21]([C:33]1[CH:38]=[CH:37][CH:36]=[CH:35][CH:34]=1)[C:22]([O:24][C@@H:25]1[CH:30]2[CH2:31][CH2:32][N+:27]([CH2:2][C:3]([C:5]3[CH:10]=[CH:9][CH:8]=[CH:7][C:6]=3[O:11][CH3:12])=[O:4])([CH2:28][CH2:29]2)[CH2:26]1)=[O:23])=[O:19])([CH3:16])([CH3:14])[CH3:15]

Participants

4

Reactant 2

HCID 123440Bromomethyl 2-methoxyphenyl ketoneHCID 67425060(R)-quinuclidin-3-yl 2-(tert-butoxycarbonylamino)-2-phenylacetate

Product 1

HCID 86665818HCID 86665818, compoundYield 95%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

2-Bromo-1-(2-methoxyphenyl)ethanone (45.8 mg, 0.20 mmol) was added to a solution of (R)-quinuclidin-3-yl 2-(tert-butoxycarbonylamino)-2-phenylacetate (C1) (72.0 mg, 0.20 mmol) in acetonitrile (3 ml). The reaction was stirred at RT overnight. The product was collected by suction filtration to get (3R)-3-(2-(tert-butoxycarbonylamino)-2-phenylacetoxy)-1-(2-(2-methoxyphenyl)-2-oxoethyl)-1-azoniabicyclo[2.2.2]octane bromide (112 mg; 95% yield).

Workup

  1. filtrationThe product was collected by suction filtration

Sources & evidence

ORD record
ord-1bd5d609534c44dbbe138d1d89cc50f6
Source dataset
uspto-grants-2014_07
Patent number
US08772314B2

Reaction notes

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