Phenacyl bromide → (3R)-3-(2-(benzyloxycarbonylamino)-2-phenylacetoxy)-1-(2-oxo-2-phenylethyl)-1-azoniabicyclo[2.2.2]octane bromide

HRID 1619513Notes

Reaction equation

HRID 1619513 reaction equation
[CH2:1]([O:8][C:9]([NH:11][CH:12]([C:24]1[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=1)[C:13]([O:15][C@@H:16]1[CH:21]2[CH2:22][CH2:23][N:18]([CH2:19][CH2:20]2)[CH2:17]1)=[O:14])=[O:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[Br:30][CH2:31][C:32]([C:34]1[CH:39]=[CH:38][CH:37]=[CH:36][CH:35]=1)=[O:33]>CCOC(C)=O>[Br-:30].[CH2:1]([O:8][C:9]([NH:11][CH:12]([C:24]1[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=1)[C:13]([O:15][C@@H:16]1[CH:21]2[CH2:20][CH2:19][N+:18]([CH2:31][C:32](=[O:33])[C:34]3[CH:39]=[CH:38][CH:37]=[CH:36][CH:35]=3)([CH2:23][CH2:22]2)[CH2:17]1)=[O:14])=[O:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

4

Reactant 2

HCID 6259Phenacyl bromideHCID 67605836(R)-quinuclidin-3-yl 2-(benzyloxycarbonylamino)-2-phenylacetate

Product 1

HCID 86665824(3R)-3-(2-(benzyloxycarbonylamino)-2-phenylacetoxy)-1-(2-oxo-2-phenylethyl)-1-azoniabicyclo[2.2.2]octane bromideYield 85.9%

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

To a solution of (R)-quinuclidin-3-yl 2-(benzyloxycarbonylamino)-2-phenylacetate (C29) (100 mg, 0.25 mmol) in EtOAc (5 ml), was added 2-bromo-1-phenylethanone (55.5 mg, 0.28 mmol), and the reaction was stirred at RT for 15 hours. The solvent was evaporated, and the resulting crude was purified by silica gel flash chromatography (DCM/MeOH=93/7) to obtain (3R)-3-(2-(benzyloxycarbonylamino)-2-phenylacetoxy)-1-(2-oxo-2-phenylethyl)-1-azoniabicyclo[2.2.2]octane bromide (127.5 mg; 85% yield).

Workup

  1. customThe solvent was evaporated
  2. customthe resulting crude was purified by silica gel flash chromatography (DCM/MeOH=93/7)

Sources & evidence

ORD record
ord-832868ce819e42c5925cfede09345cf3
Source dataset
uspto-grants-2014_07
Patent number
US08772314B2

Reaction notes

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