反応 #710505

反応方程式

Amantadine

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

H2O

→

1-(adamantyl)guanidine

溶媒

DMF

反応条件

後処理

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

実験手順

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.

出典