Trifluoroacetic acid → 3-(Pyrrolidin-3-yloxy)pyridine

HRID 412196Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 412196
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

Komponenten

4

Edukt 2

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

Produkt 1

HCID 101542053-(Pyrrolidin-3-yloxy)pyridineAusbeute 30,4 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6344DichloromethaneLösungsmittel

Versuchsvorschrift

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+).

Aufarbeitung

  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

Quellen und Nachweise

ORD-Eintrag
ord-0c39ab77737443c1bb8ef5d05201d4ca
Quelldatensatz
uspto-grants-2003_05
Patentnummer
US06562847B1

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