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

HRID 354330Notes

Reaction equation

HRID 354330 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 90%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a stirred solution of methyl 2-[[1-(tert-butoxycarbonyl)-2-pyrrolidinyl]methyloxy]pyridine-5-carboxylate (232.3 mg, 0.691 mmol) in CH2Cl2 (4.6 mL) was added TFA (0.9 mL) at 0° C., and the reaction mixture was stirred at room temp for 2 hr. The solvent was removed under a reduced pressure and the residue was made basic by the addition of 1N NaOH. The aqueous solution was extracted with CHCl3, washed with brine, and the dried over Na2SO4. The solvent was evaporated under a reduced pressure to afford 146.2 mg (90%) methyl 2(2-pyrrolidinyl)methoxypyridine-5-carboxylate as an oil. 1H-NMR (400 MHz, CDCl3) δ1.49-1.58 (m, 1H), 1.72-2.18 (m, 3H), 2.92-3.05 (m, 2H), 3.50-3.57 (m, 1H), 3.91 (s, 3H), 4.23 (dd, J=8.0, 10.7 Hz, 1H), 4.38 (dd, J=4.4, 10.3 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 1N NaOH
  3. extractionThe aqueous solution was extracted with CHCl3
  4. washwashed with brine
  5. dry with materialthe dried over Na2SO4
  6. customThe solvent was evaporated under a reduced pressure

Sources & evidence

ORD record
ord-66ab1c8c5edb4753bdb72264e78fa67a
Source dataset
uspto-grants-2004_06
Patent number
US06756378B2

Reaction notes

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