Trifluoroacetic acid → 4-(Azetidine-1-carbonyl)piperidine

HRID 426084Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 426084
[N:1]1([C:5]([CH:7]2[CH2:12][CH2:11][N:10](C(OC(C)(C)C)=O)[CH2:9][CH2:8]2)=[O:6])[CH2:4][CH2:3][CH2:2]1.FC(F)(F)C(O)=O>C(Cl)Cl>[N:1]1([C:5]([CH:7]2[CH2:12][CH2:11][NH:10][CH2:9][CH2:8]2)=[O:6])[CH2:2][CH2:3][CH2:4]1

Komponenten

4

Edukt 2

HCID 6422Trifluoroacetic acidHCID 23658779tert-Butyl 4-[(azetidin-1-yl)carbonyl]piperidine-1-carboxylate

Produkt 1

HCID 236587804-(Azetidine-1-carbonyl)piperidineAusbeute 102,3 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6344DichloromethaneLösungsmittel

Versuchsvorschrift

tert-Butyl 4-(azetidin-1-ylcarbonyl)piperidine-1-carboxylate (0.50 g, 1.86 mmol) was dissolved in methylene chloride (10 mL) and to the solution was added trifluoroacetic acid (2.12 g, 18.6 mmol). The mixture was stirred at RT overnight and then the solvent was removed by evaporation. The residue was dissolved in a small amount of methanol and THF and the solution was then loaded on a cation exchange sorbent (Isolute® SCX-2; 10 g). The column washed with THF and the product was then eluted with ammonia saturated methanol. The solvent was removed by evaporation. There was obtained 0.32 g (100%) of 4-(azetidin-1-ylcarbonyl)piperidine. 1H NMR (500 MHz, CDCl3): 1.4-1.5 (m, 4H), 2.0-2.2 (m, 3H), 2.4-2.5 (m, 2H), 2.9-3.0 (d, 2H), 3.7-3.8 (t, 2H), 3.9 (s, 1H), 4.0 (t, 2H).

Aufarbeitung

  1. customthe solvent was removed by evaporation
  2. dissolutionThe residue was dissolved in a small amount of methanol and THF
  3. washThe column washed with THF
  4. washthe product was then eluted with ammonia saturated methanol
  5. customThe solvent was removed by evaporation

Quellen und Nachweise

ORD-Eintrag
ord-0a8d6dea2fee4d158928244235de5d67
Quelldatensatz
uspto-grants-2012_01
Patentnummer
US08106208B2

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