반응 #710505

반응 방정식

Amantadine

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

H2O

→

1-(adamantyl)guanidine

용매

DMF

반응 조건

후처리

1. 1
   기타the white precipitate was removed by filtration
2. 2
   세척The precipitate was washed with CH2Cl2 twice
3. 3
   추출the combined filtrate was extracted with CH2Cl2
4. 4
   세척washed with brine
5. 5
   건조dried over MgSO4
6. 6
   농축concentrated in vacuo
7. 7
   기타purified by flash chromatography
8. 8
   기타The Boc protecting group was removed by 50% TFA/CH2Cl2 for 2 h at RT
9. 9
   기타Excess TFA was removed
10. 10
    기타to give a yellow solid which
11. 11
    기타was subsequently purified by flash chromatography (0.41 g, 74% over two steps)

실험 절차

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.

출처