Trifluoroacetic acid → Methyl 3-methyl-4-(2-pyrrolidinyl)methoxybenzoate

HRID 350361Notes

Reaction equation

HRID 350361 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[CH3:25])=O)(C)(C)C.C(O)(C(F)(F)F)=O>C(Cl)Cl>[CH3:25][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 23512098Methyl-4-[1-(tert-butoxycarbonyl)-2-pyrrolidinyl]methoxy-3-methylbenzoate

Product 1

HCID 23511782Methyl 3-methyl-4-(2-pyrrolidinyl)methoxybenzoateYield 90%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a stirred solution of methyl 4-[1-(tert-butoxycarbonyl)-2-pyrrolidinyl]methyloxy-3-methylbenzoate (301.6 mg, 0.863 mmol) in CH2Cl2 (6 mL) was added TFA (1.2 mL) at 0° C., and the mixture was stirred at room temp for 1 hr. The solvent was removed under a reduced pressure, and the residue was made basic by the addition of 1 N NaOH. The mixture was extracted with CHCl3. The extract was washed with brine, dried over Na2SO4, and concentrated under a reduced pressure to afford 192.5 mg (90%) methyl 3-methyl-4-(2-pyrrolidinyl)methoxybenzoate as an oil. 1H-NMR (400 MHz, CDCl3) δ 1.58–1.65 (m, 1H), 1.78–2.00 (m, 3H), 2.24 (s, 3H), 2.97 (dt, J=6.8, 10.2 Hz, 1H), 3.05 (dt, J=5.9, 6.8 Hz, H), 3.54–3.58 (m, 1H), 3.87 (s, 3H), 3.92 (dd, J=6.3, 9.3 Hz, 1H), 3.99 (dd, J=4.9, 9.3 Hz, 1H), 6.81 (d, J=8.3 Hz, 1H), 7.83 (s, 1H), 7.85 (dd, J=2.0, 8.3 Hz, 1H); MS (FAB) m/z 250 (M++1).

Workup

  1. customThe solvent was removed under a reduced pressure
  2. additionthe residue was made basic by the addition of 1 N 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-061c7dcfed3840a4bff9a1bf7578cfed
Source dataset
uspto-grants-2007_02
Patent number
US07179819B2

Reaction notes

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