Trifluoroacetic acid → Methyl 2-(2-pyrrolidinyl)methoxypyridine-5-carboxylate

HRID 354312Notes

Reaction equation

HRID 354312 reaction equation
C(OC([N:8]1[CH2:12][CH2:11][CH2:10][CH:9]1[CH2:13][O:14][C:15]1[CH:20]=[CH:19][C:18]([C:21]([O:23][CH3:24])=[O:22])=[CH:17][N: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][O:14][C:15]1[CH:20]=[CH:19][C:18]([C:21]([O:23][CH3:24])=[O:22])=[CH:17][N:16]=1

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 23511704Methyl 2-[[1-(tert-butoxycarbonyl)-2-pyrrolidinyl]methoxy]pyridine-5-carboxylate

Product 1

HCID 23511785Methyl 2-(2-pyrrolidinyl)methoxypyridine-5-carboxylateYield 94%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a stirred solution of methyl 2-[[1-(tert-butoxycarbonyl)-2-pyrrolidinyl]methoxy]pyridine-5-carboxylate (262.5 mg, 0.870 mmol) in CH2Cl2 (5.3 mL) was added TFA (1.1 mL) at 0° C., and the resulting 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 the 1N NaOH, and extracted with CHCl3. The extract was washed with brine, dried over Na2SO4, and concentrated under a reduced pressure to afford 173.1 mg (94%) methyl 2-[(2-pyrrolidinyl)methoxy]pyridine-5-carboxylate as a pale yellowish oil. 1H-NMR (400 MHz, CDCl3) δ1.49-1.58 (ddt, J=6.8, 8.8 Hz, 1H), 1.72-1.87 (m, 2H), 1.90-1.99 (m, 1H), 2.92-3.05 (m, 2H), 3.50-3.57 (ddd, J=4.4, 7.3, 15.1 Hz, 1H), 3.91 (s, 3H), 4.23 (dd, J=7.8, 10.7 Hz, 1H), 4.38 (dd, J=4.4, 10.7 Hz, 1H), 6.78 (d, J=8.8 Hz, 1H), 8.15 (dd, J 2.4, 8.8 Hz, 1H), 8.80 (d, J=2.4 Hz, 1H); MS (FAB) m/z 237 (M+1).

Workup

  1. customThe solvent was removed under a reduced pressure
  2. additionthe residue was made basic by the addition of the 1N NaOH
  3. extractionextracted 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-f73f8f80be37487ab63b374f94016db6
Source dataset
uspto-grants-2004_06
Patent number
US06756378B2

Reaction notes

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