Reaktion #428981

Reaktionsgleichung

4-(N-tert-butyloxycarbonylaminomethyl) piperidine

N-benzyloxycarbonyl-S-methylisothiourea

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title product

Ausbeute 37.0%

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

Ausbeute 37.0%

Lösungsmittel

ethanol

Reaktionsbedingungen

Aufarbeitung

1. 1
   TemperaturThe mixture was heated at 60°-70° C. for six hours
2. 2
   SonstigeThe solvent was evaporated
3. 3
   workup.DISSOLUTIONthe residue was dissolved in CH2C2
4. 4
   WaschenThe organic layer was washed twice with 0.3M KHSO4 and once with brine
5. 5
   TrocknenThe combined organic layer was dried (Na2SO4)
6. 6
   Filtrationfiltered
7. 7
   Sonstigeevaporated
8. 8
   SonstigeThe crude product was purified by flash chromatography

Vorschrift

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 CH2C2. 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.

Quelle