Ethyl Acetate → Methyl 2-(4-(4'-aminobiphenyl-4-yl)-2-oxabicyclo[2.2.2]octan-1-yl)acetate

HRID 881725Notes

Reaction equation

HRID 881725 reaction equation
[N+:1]([C:4]1[CH:9]=[CH:8][C:7]([C:10]2[CH:15]=[CH:14][C:13]([C:16]34[CH2:23][CH2:22][C:19]([CH2:24][C:25]([O:27][CH3:28])=[O:26])([CH2:20][CH2:21]3)[O:18][CH2:17]4)=[CH:12][CH:11]=2)=[CH:6][CH:5]=1)([O-])=O.CCOC(C)=O.[H][H]>[OH-].[OH-].[Pd+2].CO>[NH2:1][C:4]1[CH:5]=[CH:6][C:7]([C:10]2[CH:11]=[CH:12][C:13]([C:16]34[CH2:21][CH2:20][C:19]([CH2:24][C:25]([O:27][CH3:28])=[O:26])([CH2:22][CH2:23]3)[O:18][CH2:17]4)=[CH:14][CH:15]=2)=[CH:8][CH:9]=1

Participants

6

Reactant 3

HCID 8857Ethyl AcetateHCID 86700831Methyl 2-(4-(4'-nitrobiphenyl-4-yl)-2-oxabicyclo[2.2.2]octan-1-yl)acetateHCID 178418361HCID 178418361, compound

Product 1

HCID 86700832Methyl 2-(4-(4'-aminobiphenyl-4-yl)-2-oxabicyclo[2.2.2]octan-1-yl)acetateYield 90%

Reagents, catalysts & solvents 2

HCID 9942167Palladium hydroxideCatalystHCID 887MethanolSolvent

Procedure

To a round bottom flask containing methyl 2-(4-(4′-nitrobiphenyl-4-yl)-2-oxabicyclo[2.2.2]octan-1-yl)acetate (716 mg, 1.88 mmol) was added Pd(OH)2 on activated carbon (395 mg, 2.82 mmol). EtOAc (15 ml) and MeOH (3 ml) were added and the mixture was stirred under 1 atm. of hydrogen at room temperature for 2 hours. The resulting mixture was filtered through a pad of celite and concentrated to afford a crude residue. Column purification affords the title compound as off-white solid after drying (595 mg, 90% yield). LC/MS, ESI-MS(+): 352.3, RT: 1.29 (Condition E).

Workup

  1. filtrationThe resulting mixture was filtered through a pad of celite
  2. concentrationconcentrated
  3. customto afford a crude residue
  4. customColumn purification

Sources & evidence

ORD record
ord-363d286f006846f097f32c214de9a159
Source dataset
uspto-grants-2015_03
Patent number
US08993619B2

Reaction notes

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