Reacción #1951064

Ecuación de reacción

material

1-benzyl-4-(cyclopropylmethyl)-[1,4]azaphosphinane 4-oxide

HCl

→

cyclopropylmethyl-[1,4]azaphosphinane 4-oxide hydrochloride

Rendimiento 92.0%

Disolventes

ethanol

Condiciones de reacción

Tratamiento posterior

1. 1
   OtroThe solution was degassed with a stream of nitrogen and palladium on carbon (10%, 1.0 g)
2. 2
   workup.ADDITIONwas added
3. 3
   Otrowas hydrogenated on a Parr shaker overnight at 20 psi
4. 4
   FiltraciónThe reaction mixture was filtered through Celite
5. 5
   Otrothe solvents were removed under reduced pressure
6. 6
   workup.DISSOLUTIONThe product was dissolved in methanol
7. 7
   workup.ADDITIONbenzene was added
8. 8
   OtroThe solvents were removed by rotary evaporation
9. 9
   OtroThe product was recrystallized from ethanol/diethyl ether

Procedimiento

The material from Step 5 was dissolved in ethanol (80 mL) and aqueous HCl (40 mL, 1 M) was added. The solution was degassed with a stream of nitrogen and palladium on carbon (10%, 1.0 g) was added. The mixture was hydrogenated on a Parr shaker overnight at 20 psi. The reaction mixture was filtered through Celite and the solvents were removed under reduced pressure. The product was dissolved in methanol, and benzene was added. The solvents were removed by rotary evaporation. The product was recrystallized from ethanol/diethyl ether to yield 3.526 g of 4-(cyclopropylmethyl-[1,4]azaphosphinane 4-oxide hydrochloride (16.83 mmol, 92%) as a white crystalline solid. 1H NMR (400 MHz, DMSO) 9.60-9.30 (d, 2H); 3.42-3.29 (m, 4H); 2.32-2.21 (m, 2H); 2.16-2.03 (m, 2H); 1.91-1.85 (d of d, 2H); 0.95-0.85 (m, 1H); 0.59-0.51 (m, 2H); 0.26-0.20 (m, 2H); ESMS (m/z): (M+1)+found, 174; (M+23)+ found, 196.

Fuente