Trifluoroacetic acid → 3-(3-Pyrrolidinyloxy)pyridine

HRID 412196Notes

Reaction equation

HRID 412196 reaction equation
C(OC([N:8]1[CH2:12][CH2:11][CH:10]([O:13][C:14]2[CH:15]=[N:16][CH:17]=[CH:18][CH:19]=2)[CH2:9]1)=O)(C)(C)C.C(O)(C(F)(F)F)=O>C(Cl)Cl>[NH:8]1[CH2:12][CH2:11][CH:10]([O:13][C:14]2[CH:15]=[N:16][CH:17]=[CH:18][CH:19]=2)[CH2:9]1

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 10801570tert-Butyl 3-(pyridin-3-yloxy)pyrrolidine-1-carboxylate

Product 1

HCID 101542053-(3-Pyrrolidinyloxy)pyridineYield 30.4%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To 1.3 gm of 3-(1-t-butoxycarbonyl-3-pyrrolidinyloxy)-pyridine was added 10 mL of solution containing 5 mL of TFA and 5 mL of CH2Cl2 at ice-bath temperature. The reaction solution was slowly warmed to room temperature and allowed to stir 50 min at room temperature. After 50 min, solvents were removed in vacuo and the crude product was purified by flash chromatography (9:1:0.05, CHCl3:MeOH:conc. NH4OH) to obtain 120 mg (30.4% yield in two steps) of a clear oil: 1H NMR (300 MHz, CD3OD) δ8.21 (1H, d, J=2.6 Hz), 8.11 (1H, d, J=4.7 Hz), 7.38 (2H, m), 5.00 (1H, m), 3.13-2.88 (4H, m), 2.20-1.95 (2H, m); Mass spectrum (ESI) m/z 165.6 (M+H+).

Workup

  1. waitAfter 50 min
  2. customsolvents were removed in vacuo
  3. customthe crude product was purified by flash chromatography (9:1:0.05, CHCl3:MeOH:conc. NH4OH)
  4. customto obtain 120 mg (30.4% yield in two steps) of a clear oil

Sources & evidence

ORD record
ord-0c39ab77737443c1bb8ef5d05201d4ca
Source dataset
uspto-grants-2003_05
Patent number
US06562847B1

Reaction notes

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