Phenacyl bromide → HCID 86665852, compound

HRID 1619553Notes

Reaction equation

HRID 1619553 reaction equation
[CH3:1][S:2]([NH:5][CH:6]([C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1)[C:7]([O:9][C@@H:10]1[CH:15]2[CH2:16][CH2:17][N:12]([CH2:13][CH2:14]2)[CH2:11]1)=[O:8])(=[O:4])=[O:3].[Br:24][CH2:25][C:26]([C:28]1[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=1)=[O:27]>CCOC(C)=O.C(#N)C>[Br-:24].[CH3:1][S:2]([NH:5][CH:6]([C:18]1[CH:19]=[CH:20][CH:21]=[CH:22][CH:23]=1)[C:7]([O:9][C@@H:10]1[CH:15]2[CH2:14][CH2:13][N+:12]([CH2:25][C:26](=[O:27])[C:28]3[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=3)([CH2:17][CH2:16]2)[CH2:11]1)=[O:8])(=[O:3])=[O:4]

Participants

5

Reactant 2

HCID 6259Phenacyl bromideHCID 67606159HCID 67606159, compound

Product 1

HCID 86665852HCID 86665852, compoundYield 67.7%

Reagents, catalysts & solvents 2

HCID 6342AcetonitrileSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a solution of (R)-quinuclidin-3-yl 2-(methylsulfonamido)-2-phenylacetate (C76) (38.9 mg, 0.11 mmol) in EtOAc (1 ml) and acetonitrile (0.5 ml), was added 2-bromo-1-phenylethanone (25.2 mg, 0.13 mmol). The mixture was stirred at RT for 2 hours, and then the solvent was evaporated. The crude was triturated with Et2O to obtain (3R)-3-(2-(methylsulfonamido)-2-phenylacetoxy)-1-(2-oxo-2-phenylethyl)-1-azoniabicyclo[2.2.2]octane bromide (40 mg; 64.7% yield).

Workup

  1. customthe solvent was evaporated
  2. customThe crude was triturated with Et2O

Sources & evidence

ORD record
ord-e589d0fca985443997c78efca41f11c6
Source dataset
uspto-grants-2014_07
Patent number
US08772314B2

Reaction notes

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