Phenacyl bromide → HCID 86665834, compound

HRID 1619525Notes

Reaction equation

HRID 1619525 reaction equation
[C:1]([O:5][C:6]([NH:8][CH:9]([C:21]1[CH:26]=[CH:25][C:24]([CH3:27])=[CH:23][CH:22]=1)[C:10]([O:12][C@@H:13]1[CH:18]2[CH2:19][CH2:20][N:15]([CH2:16][CH2:17]2)[CH2:14]1)=[O:11])=[O:7])([CH3:4])([CH3:3])[CH3:2].[Br:28][CH2:29][C:30]([C:32]1[CH:37]=[CH:36][CH:35]=[CH:34][CH:33]=1)=[O:31]>CCOC(C)=O>[Br-:28].[C:1]([O:5][C:6]([NH:8][CH:9]([C:21]1[CH:26]=[CH:25][C:24]([CH3:27])=[CH:23][CH:22]=1)[C:10]([O:12][C@@H:13]1[CH:18]2[CH2:17][CH2:16][N+:15]([CH2:29][C:30](=[O:31])[C:32]3[CH:37]=[CH:36][CH:35]=[CH:34][CH:33]=3)([CH2:20][CH2:19]2)[CH2:14]1)=[O:11])=[O:7])([CH3:4])([CH3:3])[CH3:2]

Participants

4

Reactant 2

HCID 6259Phenacyl bromideHCID 67607092HCID 67607092, compound

Product 1

HCID 86665834HCID 86665834, compoundYield 62%

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

To a solution of (R)-quinuclidin-3-yl 2-(tert-butoxycarbonylamino)-2-p-tolylacetate (C41) (100 mg, 0.27 mmol) in EtOAc (3 ml), was added 2-bromo-1-phenylethanone (58.5 mg, 0.29 mmol), and the reaction was stirred at RT for 36 hours. The solvent was evaporated, and the residue was first triturated with i-Pr2O and then purified by flash chromatography (DCM/MeOH=95/5 to 9/1) to obtain (3R)-3-(2-(tert-butoxycarbonylamino)-2-p-tolylacetoxy)-1-(2-oxo-2-phenylethyl)-1-azoniabicyclo[2.2.2]octane bromide (94.4 mg; 62% yield).

Workup

  1. customThe solvent was evaporated
  2. customthe residue was first triturated with i-Pr2O
  3. custompurified by flash chromatography (DCM/MeOH=95/5 to 9/1)

Sources & evidence

ORD record
ord-edbfa9e90772407eaa65c424f76e3ef5
Source dataset
uspto-grants-2014_07
Patent number
US08772314B2

Reaction notes

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