2-Bromo-1-(4-hydroxyphenyl)ethanone → HCID 86660310, compound

HRID 453700Notes

Reaction equation

HRID 453700 reaction equation
[Br:1][CH2:2][C:3]([C:5]1[CH:10]=[CH:9][C:8]([OH:11])=[CH:7][CH:6]=1)=[O:4].[C:12]1([C@@H:18]([NH:30][C:31]2[CH:36]=[CH:35][CH:34]=[CH:33][CH:32]=2)[C:19]([O:21][C@@H:22]2[CH:27]3[CH2:28][CH2:29][N:24]([CH2:25][CH2:26]3)[CH2:23]2)=[O:20])[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1>CCOC(C)=O>[Br-:1].[OH:11][C:8]1[CH:9]=[CH:10][C:5]([C:3](=[O:4])[CH2:2][N+:24]23[CH2:25][CH2:26][CH:27]([CH2:28][CH2:29]2)[C@@H:22]([O:21][C:19](=[O:20])[C@@H:18]([C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=2)[NH:30][C:31]2[CH:36]=[CH:35][CH:34]=[CH:33][CH:32]=2)[CH2:23]3)=[CH:6][CH:7]=1

Participants

4

Reactant 2

HCID 49642-Bromo-1-(4-hydroxyphenyl)ethanoneHCID 46840261(R)-((R)-quinuclidin-3-yl) 2-phenyl-2-(phenylamino)acetate

Product 1

HCID 86660310HCID 86660310, compoundYield 100%

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

2-Bromo-1-(4-hydroxyphenyl)ethanone (256 mg, 1.19 mmol) was added to a solution of (R)—((R)-quinuclidin-3-yl) 2-phenyl-2-(phenylamino)acetate (diastereomer 1 of I2) (400 mg, 1.19 mmol) in EtOAc (15 ml). The resulting reaction was stirred at room temperature for 15 hours. The solvent was removed under vacuum, and the residue was triturated with Et2O to obtain (R)-1-(2-(4-hydroxyphenyl)-2-oxoethyl)-3-((R)-2-phenyl-2-(phenylamino)acetoxy)-1-azoniabicyclo[2.2.2]octane bromide (655 mg, 100% yield).

Workup

  1. customThe resulting reaction
  2. customThe solvent was removed under vacuum
  3. customthe residue was triturated with Et2O

Sources & evidence

ORD record
ord-6b67841b5d134defbc26f72d2c31b55e
Source dataset
uspto-grants-2013_07
Patent number
US08492548B2

Reaction notes

Loading…