Réaction #954

Équation de réaction

4-(N-tert-butyloxycarbonylaminomethyl) piperidine

N-benzyloxycarbonyl-S-methylisothiourea

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title product

Rendement 37.0%

4-(N-tert-butyloxycarbonylaminomethyl)-1-(N-benzyloxycarbon ylamidino) piperidine

Rendement 37.0%

Solvants

ethanol

Conditions de réaction

Traitement

1. 1
   TempératureThe mixture was heated at 60°-70° C. for six hours
2. 2
   AutreThe solvent was evaporated
3. 3
   workup.DISSOLUTIONthe residue was dissolved in CH2Cl2
4. 4
   LavageThe organic layer was washed twice with 0.3M KHSO4 and once with brine
5. 5
   SéchageThe combined organic layer was dried (Na2SO4)
6. 6
   Filtrationfiltered
7. 7
   Autreevaporated
8. 8
   AutreThe crude product was purified by flash chromatography

Mode opératoire

7.8 g (36.4 mmole) of 4-(N-tert-butyloxycarbonylaminomethyl) piperidine and 8.98 g (40 mmole) of N-benzyloxycarbonyl-S-methylisothiourea was mixed in 25 mL ethanol. The mixture was heated at 60°-70° C. for six hours and left at room temperature for two days. The solvent was evaporated and the residue was dissolved in CH2Cl2. The organic layer was washed twice with 0.3M KHSO4 and once with brine. The combined organic layer was dried (Na2SO4), filtered and evaporated. The crude product was purified by flash chromatography using a stepwise gradient of CH2Cl2 /MeOH (100/0, 97/3, 95/5, 90/10) as eluent to yield 5.22 g (37%) of the title product.

Source