反応 #1951064

反応方程式

material

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

HCl

→

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

収率 92.0%

溶媒

ethanol

反応条件

後処理

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

実験手順

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.

出典