Trifluoroacetic acid → HCID 23511940, compound

HRID 354332Notes

Reaction equation

HRID 354332 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 1N 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 1N 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-1a13ba1479e04c88abd0fd9dcc266d29
Source dataset
uspto-grants-2004_06
Patent number
US06756378B2

Reaction notes

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