تفاعل #710505

معادلة التفاعل

Amantadine

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

H2O

→

1-(adamantyl)guanidine

المذيبات

DMF

ظروف التفاعل

المعالجة

1. 1
   أخرىthe white precipitate was removed by filtration
2. 2
   غسيلThe precipitate was washed with CH2Cl2 twice
3. 3
   استخلاصthe combined filtrate was extracted with CH2Cl2
4. 4
   غسيلwashed with brine
5. 5
   تجفيفdried over MgSO4
6. 6
   تركيزconcentrated in vacuo
7. 7
   أخرىpurified by flash chromatography
8. 8
   أخرىThe Boc protecting group was removed by 50% TFA/CH2Cl2 for 2 h at RT
9. 9
   أخرىExcess TFA was removed
10. 10
    أخرىto give a yellow solid which
11. 11
    أخرىwas subsequently purified by flash chromatography (0.41 g, 74% over two steps)

الإجراء التجريبي

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.

المصدر