Reacción #10309

Ecuación de reacción

hydrochloric acid

1-(Diphenylmethyl)-3-{[(2-fluorophenyl)sulfonyl]methyl}azetidine

hydrogen

→

title compound

Rendimiento 91.0%

3-{[(2-Fluorophenyl)sulfonyl]methyl}azetidine hydrochloride

Rendimiento 91.0%

Disolventes

water

ethanol

Condiciones de reacción

Tratamiento posterior

1. 1
   OtroThe catalyst was removed by filtration
2. 2
   Concentraciónthe filtrate concentrated to a small volume
3. 3
   workup.DISSOLUTIONThe solid present was redissolved
4. 4
   workup.ADDITIONby adding ethanol
5. 5
   Filtraciónthe solution filtered
6. 6
   ConcentraciónThe filtrate was concentrated to a small volume once again
7. 7
   Otroto give a crystalline solid which
8. 8
   Otrowas collected under suction
9. 9
   Lavadowashed with cold ethanol
10. 10
    Otrodried in vacuo

Procedimiento

1-(Diphenylmethyl)-3-{[(2-fluorophenyl)sulfonyl]methyl}azetidine (1.33 g, 3.37 mmol) was dissolved in ethanol (80 mL). The solution was diluted with 2M hydrochloric acid (1.8 mL) and water (20 mL). 20% Palladium hydroxide on carbon (0.63 g) was added and the mixture shaken on a Parr apparatus under 50 psi of hydrogen for 3.5 h. The catalyst was removed by filtration and the filtrate concentrated to a small volume. The solid present was redissolved by adding ethanol and the solution filtered. The filtrate was concentrated to a small volume once again to give a crystalline solid which was collected under suction, washed with cold ethanol and dried in vacuo to afford the title compound as colourless crystals (0.81 g, 91%); 1H NMR (500 MHz, CD3OD) δ 3.34–3.42 (1H, m), 3.80 (2H, d, J=7.6 Hz), 4.07 (2H, t, J=10 Hz), 4.14 (2H, t, J=10 Hz), 7.41–7.49 (2H, m), 7.80–7.84 (1H, m), 7.90–7.92 (1H, m); 19F NMR (471 MHz, CD3OD) δ −110.6; m/z (ES+) 230 ([M+H]+, 100%).

Fuente