反应 #1951064

反应方程式

material

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

HCl

→

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

收率 92.0%

溶剂

ethanol

反应条件

后处理

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

实验过程

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.

来源