Trifluoroacetic acid → HCID 23512385, compound

HRID 354309Notes

Reaction equation

HRID 354309 reaction equation
C(OC([N:8]1[CH2:12][CH2:11][CH2:10][CH:9]1[CH2:13][O:14][C:15]1[CH:24]=[CH:23][C:18]([C:19]([O:21][CH3:22])=[O:20])=[CH:17][C:16]=1[F:25])=O)(C)(C)C.C(O)(C(F)(F)F)=O>C(Cl)Cl>[F:25][C:16]1[CH:17]=[C:18]([CH:23]=[CH:24][C:15]=1[O:14][CH2:13][CH:9]1[CH2:10][CH2:11][CH2:12][NH:8]1)[C:19]([O:21][CH3:22])=[O:20]

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 23512180Methyl 4-[1-(tert-butoxycarbonyl)-2-pyrrolidinyl]methoxy-3-fluorobenzoate

Product 1

HCID 23512385HCID 23512385, compoundYield 76%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a stirred solution of methyl 4-[1-(tert-butoxycarbonyl)-2-pyrrolidinyl]methoxy-3-fluorobenzoate (323.0 mg, 0.914 mmol) in CH2Cl2 (6.5 mL) was added TFA (1.3 mL) at 0° C., and the mixture was stirred 1.5 hr at room temp. The solvent was removed under a reduced pressure and the residue was made basic by the addition of 1N NaOH. The mixture was extracted with CHCl3. The extract was washed with brine, dried over Na2SO4, and concentrated under a reduced pressure to afford 174.8 mg (76%) methyl 3-fluoro-4-(2-pyrrolidinyl)methoxybenzoate as a brownish oil. 1H-NMR (400 MHz, CDCl3) δ1.54-1.63 (m, 1H), 1.76-2.02 (m, 3H), 2.93-3.07 (m, 2H), 3.57 (ddd, J=4.9, 6.9, 14.3 Hz, 1H), 3.89 (s, 3H), 3.97 (dd, J=6.8, 9.3 Hz, 1H), 4.04 (dd, J=5.0, 8.8 Hz, 1H), 6.98 (t, J=17.6 Hz, 1H), 7.73 (dd, J=2.0, 11.7 Hz, 1H), 7.78 (dt, J=2.0, 8.8 Hz, 1H); MS (FAB) m/z 253 (M++1).

Workup

  1. customThe solvent was removed under a reduced pressure
  2. additionthe residue was made basic by the addition of 1N NaOH
  3. extractionThe mixture was extracted with CHCl3
  4. washThe extract was washed with brine
  5. dry with materialdried over Na2SO4
  6. concentrationconcentrated under a reduced pressure

Sources & evidence

ORD record
ord-f84ee51129494139b67f8572978bae10
Source dataset
uspto-grants-2004_06
Patent number
US06756378B2

Reaction notes

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