2-Bromo-4'-nitroacetophenone → HCID 86660313, compound

HRID 453703Notes

Reaction equation

HRID 453703 reaction equation
[Br:1][CH2:2][C:3]([C:5]1[CH:10]=[CH:9][C:8]([N+:11]([O-])=O)=[CH:7][CH:6]=1)=[O:4].[C:14]1([C@@H:20]([NH:32][C:33]2[CH:38]=[CH:37][CH:36]=[CH:35][CH:34]=2)[C:21]([O:23][C@@H:24]2[CH:29]3[CH2:30][CH2:31][N:26]([CH2:27][CH2:28]3)[CH2:25]2)=[O:22])[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1>CCOC(C)=O.CO.[Pd]>[Br-:1].[NH2:11][C:8]1[CH:9]=[CH:10][C:5]([C:3](=[O:4])[CH2:2][N+:26]23[CH2:27][CH2:28][CH:29]([CH2:30][CH2:31]2)[C@@H:24]([O:23][C:21](=[O:22])[C@@H:20]([C:14]2[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=2)[NH:32][C:33]2[CH:38]=[CH:37][CH:36]=[CH:35][CH:34]=2)[CH2:25]3)=[CH:6][CH:7]=1

Participants

6

Reactant 2

HCID 668402-Bromo-4'-nitroacetophenoneHCID 46840261(R)-((R)-quinuclidin-3-yl) 2-phenyl-2-(phenylamino)acetate

Product 1

HCID 86660313HCID 86660313, compoundYield 97%

Reagents, catalysts & solvents 3

HCID 23938PalladiumCatalystHCID 887MethanolSolventHCID 8857Ethyl AcetateSolvent

Procedure

2-Bromo-1-(4-nitrophenyl)ethanone (290 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 reaction mixture was stirred at room temperature for 2 hours. The reaction mixture was poured into a Parr's vial and diluted with MeOH. Pd/C (cat amount; about 10 mg) was added, and reaction is hydrogenated at 35 pound per square inch (psi) for 8 hours (UPLC-MS: complete conversion). The catalyst was removed by filtration, and the clear solution was concentrated under vacuum. The residue was triturated with Et2O and filtered to obtain (R)-1-(2-(4-aminophenyl)-2-oxoethyl)-3-((R)-2-phenyl-2-(phenylamino)acetoxy)-1-azoniabicyclo[2.2.2]octane bromide (632 mg, 97% yield).

Workup

  1. additionThe reaction mixture was poured into a Parr's vial
  2. customreaction
  3. waitis hydrogenated at 35 pound per square inch (psi) for 8 hours
  4. customThe catalyst was removed by filtration
  5. concentrationthe clear solution was concentrated under vacuum
  6. customThe residue was triturated with Et2O
  7. filtrationfiltered

Sources & evidence

ORD record
ord-d6aff25199de4cc2a687c9ae6e804327
Source dataset
uspto-grants-2013_07
Patent number
US08492548B2

Reaction notes

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