Ammonium formate → 1-Azetidin-3-yl-4-(azetidin-1-ylcarbonyl)piperidine

Temperatur

120 °C

4-(Azetidin-1-ylcarbonyl)-1-[1-(diphenylmethyl)azetidin-3-yl]piperidine (0.42 g, 1.1 mmol) was dissolved in ethanol and to the resultant solution was added palladium hydroxide on carbon (0.15 g) and ammonium formate (0.28 g, 4.4 mmol). The reaction mixture was heated for 4 min at 120° C. using microwave single node heating. The catalyst was filtered off by means of a phase separator and the filter cake washed with ethanol. The solvent was removed by evaporation and the residue was dissolved in methanol (1 mL) and THF (10 mL). The solution was 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 and there was obtained 0.25 g of the title compound as colourless oil. 1H NMR (500 MHz, CD3OD): 2.0-2.2 (m, 4H), 2.3-2.4 (m, 2H), 2.6-2.8 (m, 3H), 3.2-3.3 (d, 2H), 3.8 (qn, 1H), 4.3 (t, 2H), 4.4 (m, 2H), 4.5 (m, 2H), 4.6 (t, 2H); LCMS: m/z 224 (M+1)+.

1. temperatureheating
2. filtrationThe catalyst was filtered off by means of a phase separator
3. washthe filter cake washed with ethanol
4. customThe solvent was removed by evaporation
5. dissolutionthe residue was dissolved in methanol (1 mL)
6. washThe column washed with THF
7. washthe product was then eluted with ammonia saturated methanol
8. customThe solvent was removed by evaporation

ORD-Eintrag

ord-ec88521b117c4805966619ac89121af8

Quelldatensatz

uspto-grants-2012_01

DOI

10.6084/m9.figshare.5104873.v1

Patentnummer

US08106208B2