Trifluoroacetic acid → 6-Aminobicyclo(2.2.1)heptane-2-carboxylic acid

HRID 75048Notes

Reaction equation

HRID 75048 reaction equation
C(OC([NH:8][CH:9]1[CH:14]2[CH2:15][CH:11]([CH2:12][CH:13]2[C:16]([OH:18])=[O:17])[CH2:10]1)=O)(C)(C)C.FC(F)(F)C(O)=O>ClCCl>[NH2:8][CH:9]1[CH:14]2[CH2:15][CH:11]([CH2:12][CH:13]2[C:16]([OH:18])=[O:17])[CH2:10]1

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 672859386-(Tert-butoxycarbonylamino)norbornane-2-carboxylic acid

Product 1

HCID 206527796-Aminobicyclo(2.2.1)heptane-2-carboxylic acid

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A solution of 6-(tert-butoxycarbonylamino)norbornane-2-carboxylic acid, 72g, in dichloromethane (5 mL) was treated with trifluoroacetic acid (5 mL) for 1 hour at room temperature. The solvent was evaporated under reduced pressure and the resulting product was dissolved in 2 mL TFA and added to a stirring 1N HCl in Et2O solution. After stirring the mixture for 0.5 hour, the resulting precipitate was filtered and washed with dry Et2O to give 6-aminobicyclo[2.2.1]heptane-2-carboxylic acid.

Workup

  1. customThe solvent was evaporated under reduced pressure
  2. dissolutionthe resulting product was dissolved in 2 mL TFA
  3. additionadded to a stirring 1N HCl in Et2O solution
  4. filtrationthe resulting precipitate was filtered
  5. washwashed with dry Et2O

Sources & evidence

ORD record
ord-4b0fdd6dfffd4308abcea748e3fcda6f
Source dataset
uspto-grants-2014_09
Patent number
US08829007B2

Reaction notes

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