反応 #954

反応方程式

4-(N-tert-butyloxycarbonylaminomethyl) piperidine

N-benzyloxycarbonyl-S-methylisothiourea

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title product

収率 37.0%

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

収率 37.0%

溶媒

ethanol

反応条件

後処理

1. 1
   温度The mixture was heated at 60°-70° C. for six hours
2. 2
   その他The solvent was evaporated
3. 3
   workup.DISSOLUTIONthe residue was dissolved in CH2Cl2
4. 4
   洗浄The organic layer was washed twice with 0.3M KHSO4 and once with brine
5. 5
   乾燥The combined organic layer was dried (Na2SO4)
6. 6
   ろ過filtered
7. 7
   その他evaporated
8. 8
   その他The crude product was purified by flash chromatography

実験手順

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.

出典