Phenacyl bromide → HCID 86660330, compound

HRID 469484Notes

Reaction equation

HRID 469484 reaction equation
[Br:1][CH2:2][C:3]([C:5]1[CH:10]=[CH:9][CH:8]=[CH:7][CH:6]=1)=[O:4].[S:11]1[CH:15]=[C:14]([CH:16]([NH:28][C:29]2[CH:34]=[CH:33][CH:32]=[CH:31][C:30]=2[CH2:35][CH3:36])[C:17]([O:19][C@@H:20]2[CH:25]3[CH2:26][CH2:27][N:22]([CH2:23][CH2:24]3)[CH2:21]2)=[O:18])[C:13]2[CH:37]=[CH:38][CH:39]=[CH:40][C:12]1=2>CCOC(C)=O>[Br-:1].[S:11]1[CH:15]=[C:14]([CH:16]([NH:28][C:29]2[CH:34]=[CH:33][CH:32]=[CH:31][C:30]=2[CH2:35][CH3:36])[C:17]([O:19][C@@H:20]2[CH:25]3[CH2:26][CH2:27][N+:22]([CH2:2][C:3](=[O:4])[C:5]4[CH:10]=[CH:9][CH:8]=[CH:7][CH:6]=4)([CH2:23][CH2:24]3)[CH2:21]2)=[O:18])[C:13]2[CH:37]=[CH:38][CH:39]=[CH:40][C:12]1=2

Participants

4

Reactant 2

HCID 6259Phenacyl bromide2×HCID 58557024HCID 58557024, compound

Product 1

HCID 86660330HCID 86660330, compoundYield 36%

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Conditions

Temperature
100 °C

Procedure

A mixture of 2-bromo-1-phenylethanone (44.8 mg, 0.22 mmol) and (R)-quinuclidin-3-yl 2-(benzo[b]thiophen-3-yl)-2-(2-ethylphenylamino)acetate (C44) (86 mg, 0.20 mmol) in EtOAc (3 ml) was heated under microwave irradiation at 100° C. for 1 hour. 2-Bromo-1-phenylethanone (44.8 mg, 0.22 mmol) was added, and the mixture was heated at 100° C. under microwave irradiation for an additional hour. The solvent was evaporated, and the crude product was triturated with Et2O to collect (3R)-3-(2-(benzo[b]thiophen-3-yl)-2-(2-ethylphenylamino)acetoxy)-1-(2-oxo-2-phenylethyl)-1-azoniabicyclo[2.2.2]octane bromide (44.6 mg, 35.2% yield).

Workup

  1. temperaturethe mixture was heated at 100° C. under microwave irradiation for an additional hour
  2. customThe solvent was evaporated
  3. customthe crude product was triturated with Et2O

Sources & evidence

ORD record
ord-e7baa2d09d524934aba91a9a77444ca8
Source dataset
uspto-grants-2014_01
Patent number
US08629160B2

Reaction notes

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