Trifluoroacetic acid → 3-[(3,4-Dichlorophenyl)methyl]-8-azabicyclo[3.2.1]octane

HRID 1793644Notes

Reaction equation

HRID 1793644 reaction equation
C(OC([N:8]1[CH:13]2[CH2:14][CH2:15][CH:9]1[CH2:10][CH:11]([CH2:16][C:17]1[CH:22]=[CH:21][C:20]([Cl:23])=[C:19]([Cl:24])[CH:18]=1)[CH2:12]2)=O)(C)(C)C.C(O)(C(F)(F)F)=O>C(Cl)Cl>[Cl:24][C:19]1[CH:18]=[C:17]([CH:22]=[CH:21][C:20]=1[Cl:23])[CH2:16][CH:11]1[CH2:10][CH:9]2[NH:8][CH:13]([CH2:14][CH2:15]2)[CH2:12]1

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 69593412HCID 69593412, compound

Product 1

HCID 220228273-[(3,4-Dichlorophenyl)methyl]-8-azabicyclo[3.2.1]octaneYield 98.4%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

3-(3,4-Dichloro-benzyl)-8-aza-bicyclo[3.2.1]octane-8-carboxylic acid tert-butyl ester (0.35 g, 0.94 mmol) was stirred in 2 mL of CH2Cl2 with 0.5 mL of TFA at rt for 3 h. After being quenched with 20% NaOH to basic medium, the mixture was extracted with EtOAc. The organic layer was washed with NaCl (sat.), dried over Na2SO4 and concentrated to give 0.25 g of 3-(3,4-Dichloro-benzyl)-8-aza-bicyclo[3.2.1]octane.

Workup

  1. customAfter being quenched with 20% NaOH to basic medium
  2. extractionthe mixture was extracted with EtOAc
  3. washThe organic layer was washed with NaCl (sat.)
  4. dry with materialdried over Na2SO4
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-cc5d6d3efe544eaeb49452f7c8ca9b47
Source dataset
uspto-grants-2006_07
Patent number
US07081531B2

Reaction notes

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