Trifluoroacetic acid → HCID 23511940, compound

HRID 350395Notes

Reaction equation

HRID 350395 reaction equation
C(OC([N:8]1[CH2:12][CH2:11][CH2:10][CH:9]1[CH2:13][NH:14][C:15]1[CH:24]=[CH:23][C:18]([C:19]([O:21][CH3:22])=[O:20])=[CH:17][CH:16]=1)=O)(C)(C)C.C(O)(C(F)(F)F)=O>C(Cl)Cl>[NH:8]1[CH2:12][CH2:11][CH2:10][CH:9]1[CH2:13][NH:14][C:15]1[CH:24]=[CH:23][C:18]([C:19]([O:21][CH3:22])=[O:20])=[CH:17][CH:16]=1

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 693323161,1-Dimethylethyl 2-[[[4-(methoxycarbonyl)phenyl]amino]methyl]-1-pyrrolidinecarboxylate

Product 1

HCID 23511940HCID 23511940, compoundYield 88.1%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a stirred solution of methyl 4-[1-(tert-butoxycarbonyl)-2-pyrrolidinylmethylamino]benzoate (2.17 g, 6.490 mmol) in CH2Cl2 (44 mL) was added TFA (8.7 mL) at 0° C., and the resulting mixture was stirred overnight at room temp. The solvent was removed under a reduced pressure and the residue was treated with 1 N NaOH. The mixture was extracted with CH2Cl2. The extract was washed with brine, dried over Na2SO4, and the solvent was concentrated under a reduced pressure to afford 1.34 g (88%) methyl 4-(2-pyrrolidinylmethylamino)benzoate as a brown oil, which is used to the subsequent reaction without further purification.

Workup

  1. customThe solvent was removed under a reduced pressure
  2. additionthe residue was treated with 1 N NaOH
  3. extractionThe mixture was extracted with CH2Cl2
  4. washThe extract was washed with brine
  5. dry with materialdried over Na2SO4
  6. concentrationthe solvent was concentrated under a reduced pressure

Sources & evidence

ORD record
ord-a7bc3fb8aeeb4fd5a647de4af419ba2a
Source dataset
uspto-grants-2007_02
Patent number
US07179819B2

Reaction notes

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