Reaction #710505

Reaction equation

Amantadine

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

H2O

→

1-(adamantyl)guanidine

Solvents

DMF

Conditions

Workup

1. 1
   Otherthe white precipitate was removed by filtration
2. 2
   WashThe precipitate was washed with CH2Cl2 twice
3. 3
   Extractionthe combined filtrate was extracted with CH2Cl2
4. 4
   Washwashed with brine
5. 5
   Dryingdried over MgSO4
6. 6
   Concentrationconcentrated in vacuo
7. 7
   Otherpurified by flash chromatography
8. 8
   OtherThe Boc protecting group was removed by 50% TFA/CH2Cl2 for 2 h at RT
9. 9
   OtherExcess TFA was removed
10. 10
    Otherto give a yellow solid which
11. 11
    Otherwas subsequently purified by flash chromatography (0.41 g, 74% over two steps)

Procedure

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.

Source