反应 #710505

反应方程式

Amantadine

1,3-bis(tert-butoxycarbonyl)-2-methyl-2-thiopseudourea

H2O

→

1-(adamantyl)guanidine

溶剂

DMF

反应条件

后处理

1. 1
   其他the white precipitate was removed by filtration
2. 2
   洗涤The precipitate was washed with CH2Cl2 twice
3. 3
   萃取the combined filtrate was extracted with CH2Cl2
4. 4
   洗涤washed with brine
5. 5
   干燥dried over MgSO4
6. 6
   浓缩concentrated in vacuo
7. 7
   其他purified by flash chromatography
8. 8
   其他The Boc protecting group was removed by 50% TFA/CH2Cl2 for 2 h at RT
9. 9
   其他Excess TFA was removed
10. 10
    其他to give a yellow solid which
11. 11
    其他was subsequently purified by flash chromatography (0.41 g, 74% over two steps)

实验过程

Amantadine (0.30 g, 2 mmol), HgCl2 (0.54 g, 2 mmol), and 1,3-bis(tert-butoxycarbonyl)-2-methyl-2-thiopseudourea (0.58 g, 2 mmol) were stirred in DMF (10 mL) under a N2 atmosphere for 24 h. H2O was added to the reaction mixture, and the white precipitate was removed by filtration. The precipitate was washed with CH2Cl2 twice, and the combined filtrate was extracted with CH2Cl2, washed with brine and dried over MgSO4, concentrated in vacuo, and purified by flash chromatography. The Boc protecting group was removed by 50% TFA/CH2Cl2 for 2 h at RT. Excess TFA was removed by passing N2 through the solution to give a yellow solid which was subsequently purified by flash chromatography (0.41 g, 74% over two steps). 1H-NMR (360 MHz, CD3OD) δ 2.13 (br s, 3H), 1.97 (br s, 6H), 1.76 (br s, 6H); 13C-NMR (90 MHz, CD3OD) δ 160.35, 53.83, 42.45, 36.86, 31.03; ESI-MS: Calculated for C11H19N3 (M+H)+ 194.2. Found: 194.7.

来源