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

HRID 350392Notes

Reaction equation

HRID 350392 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 1 N 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) δ 1.49–1.58 (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 1 N 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-7144aa4fc3194686888da6e42c4909a5
Source dataset
uspto-grants-2007_02
Patent number
US07179819B2

Reaction notes

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