Реакция #954

Уравнение реакции

4-(N-tert-butyloxycarbonylaminomethyl) piperidine

N-benzyloxycarbonyl-S-methylisothiourea

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title product

Выход 37.0%

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

Выход 37.0%

Растворители

ethanol

Условия реакции

Обработка

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

Методика

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.

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