Реакция #710505

Уравнение реакции

Amantadine

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

H2O

→

1-(adamantyl)guanidine

Растворители

DMF

Условия реакции

Обработка

1. 1
   Другоеthe white precipitate was removed by filtration
2. 2
   ПромывкаThe precipitate was washed with CH2Cl2 twice
3. 3
   Экстракцияthe combined filtrate was extracted with CH2Cl2
4. 4
   Промывкаwashed with brine
5. 5
   Сушкаdried over MgSO4
6. 6
   Концентрированиеconcentrated in vacuo
7. 7
   Другоеpurified by flash chromatography
8. 8
   ДругоеThe Boc protecting group was removed by 50% TFA/CH2Cl2 for 2 h at RT
9. 9
   ДругоеExcess TFA was removed
10. 10
    Другоеto give a yellow solid which
11. 11
    Другоеwas subsequently purified by flash chromatography (0.41 g, 74% over two steps)

Методика

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.

Источник