Reacción #710505

Ecuación de reacción

Amantadine

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

H2O

→

1-(adamantyl)guanidine

Disolventes

DMF

Condiciones de reacción

Tratamiento posterior

1. 1
   Otrothe white precipitate was removed by filtration
2. 2
   LavadoThe precipitate was washed with CH2Cl2 twice
3. 3
   Extracciónthe combined filtrate was extracted with CH2Cl2
4. 4
   Lavadowashed with brine
5. 5
   Secadodried over MgSO4
6. 6
   Concentraciónconcentrated in vacuo
7. 7
   Otropurified by flash chromatography
8. 8
   OtroThe Boc protecting group was removed by 50% TFA/CH2Cl2 for 2 h at RT
9. 9
   OtroExcess TFA was removed
10. 10
    Otroto give a yellow solid which
11. 11
    Otrowas subsequently purified by flash chromatography (0.41 g, 74% over two steps)

Procedimiento

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.

Fuente