Phenacyl bromide → HCID 57344855, compound

HRID 1619523Notes

Reaction equation

HRID 1619523 reaction equation
[CH:1]1([O:7][C:8]([NH:10][CH:11]([C:23]2[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=2)[C:12]([O:14][C@@H:15]2[CH:20]3[CH2:21][CH2:22][N:17]([CH2:18][CH2:19]3)[CH2:16]2)=[O:13])=[O:9])[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1.[Br:29][CH2:30][C:31]([C:33]1[CH:38]=[CH:37][CH:36]=[CH:35][CH:34]=1)=[O:32]>CCOC(C)=O>[Br-:29].[CH:1]1([O:7][C:8]([NH:10][CH:11]([C:23]2[CH:24]=[CH:25][CH:26]=[CH:27][CH:28]=2)[C:12]([O:14][C@@H:15]2[CH:20]3[CH2:19][CH2:18][N+:17]([CH2:30][C:31](=[O:32])[C:33]4[CH:38]=[CH:37][CH:36]=[CH:35][CH:34]=4)([CH2:22][CH2:21]3)[CH2:16]2)=[O:13])=[O:9])[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1

Participants

4

Reactant 2

HCID 6259Phenacyl bromideHCID 67607463HCID 67607463, compound

Product 1

HCID 57344855HCID 57344855, compoundYield 53%

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

To a solution of (R)-quinuclidin-3-yl 2-(cyclohexyloxycarbonylamino)-2-phenylacetate (C38) (105 mg, 0.27 mmol) in EtOAc (3 ml), was added 2-bromo-1-phenylethanone (59.5 mg, 0.30 mmol). The reaction was stirred at RT for 15 hours, and then the solvent was evaporated. The crude was purified by flash chromatography (DCM/MeOH=95/5 to 93/7) to obtain (3R)-3-(2-(cyclohexyloxycarbonylamino)-2-phenylacetoxy)-1-(2-oxo-2-phenylethyl)-1-azoniabicyclo[2.2.2]octane bromide (83.8 mg; 53% yield).

Workup

  1. customthe solvent was evaporated
  2. customThe crude was purified by flash chromatography (DCM/MeOH=95/5 to 93/7)

Sources & evidence

ORD record
ord-8af9e283387c4c7581e889359db42fe4
Source dataset
uspto-grants-2014_07
Patent number
US08772314B2

Reaction notes

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