Trifluoroacetic acid → 3-(3-Chloropyridin-2-yl)-3,8-diazabicyclo[3.2.1]octane

HRID 1394078Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1394078
[Cl:1][C:2]1[C:3]([N:8]2[CH2:14][CH:13]3[N:15](C(OC(C)(C)C)=O)[CH:10]([CH2:11][CH2:12]3)[CH2:9]2)=[N:4][CH:5]=[CH:6][CH:7]=1.FC(F)(F)C(O)=O>ClCCl>[Cl:1][C:2]1[C:3]([N:8]2[CH2:9][CH:10]3[NH:15][CH:13]([CH2:12][CH2:11]3)[CH2:14]2)=[N:4][CH:5]=[CH:6][CH:7]=1

Komponenten

4

Edukt 2

HCID 6422Trifluoroacetic acidHCID 21904762Tert-butyl 3-(3-chloro-2-pyridinyl)-3,8-diazabicyclo[3.2.1]octane-8-carboxylate

Produkt 1

HCID 219047683-(3-Chloropyridin-2-yl)-3,8-diazabicyclo[3.2.1]octane

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6344DichloromethaneLösungsmittel

Versuchsvorschrift

tert-Butyl 3-(3-chloro-2-pyridinyl)-3,8-diazabicyclo[3.2.1]octane-8-carboxylate (419 mg, 1.29 mmol) in dry dichloromethane (5 mL) was treated with trifluoroacetic acid and stirred at room temperature for an hour. The mixture was concentrated under reduced pressure and the residue was treated with 1N sodium hydroxide solution. The mixture was extracted with ethyl acetate and the organic phase was concentrated under reduced pressure to provide the title compound. MS (ESI) m/z: 224 (M+H)+; 1H NMR (CDCl3) δ 1.86 (m, 2H), 2.09 (m, 2H), 3.09 (d, 2H), 3.63 (m, 4H), 6.81 (dd, 1H), 7.56 (dd, 1H), 8.16 (dd, 1H).

Aufarbeitung

  1. concentrationThe mixture was concentrated under reduced pressure
  2. additionthe residue was treated with 1N sodium hydroxide solution
  3. extractionThe mixture was extracted with ethyl acetate
  4. concentrationthe organic phase was concentrated under reduced pressure

Quellen und Nachweise

ORD-Eintrag
ord-c0afab7d92194d478364834f77f076e3
Quelldatensatz
uspto-grants-2008_03
Patentnummer
US07348343B2

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