반응 #67699

반응 방정식

trans-(4-Amino-tetrahydro-pyran-3-yl)-carbamic acid tert-butyl ester

intermediate G

trans-(4-Amino-tetrahydro-pyran-3-yl)-carbamic acid tert-butyl ester

Potassium carbonate

1,4-dibromobutane

→

title compound

수율 84.0%

trans-(4-Pyrrolidin-1-yl-tetrahydro-pyran-3-yl)-carbamic acid tert-butyl ester

수율 84.0%

용매

acetonitrile

반응 조건

후처리

1. 1
   온도the reaction mixture was refluxed overnight
2. 2
   기타The solvent was evaporated off
3. 3
   추출extracted three times with diethylether
4. 4
   기타The combined organic phases were dried on sodium sulfate
5. 5
   여과filtered
6. 6
   기타evaporated
7. 7
   기타Purification of the residue by flash chromatography on silica gel (dichloromethane/methanol/ammonia 1:0:0→140:10:1)

실험 절차

trans-(4-Amino-tetrahydro-pyran-3-yl)-carbamic acid tert-butyl ester (intermediate G, 330 mg, 1.53 mmol) was dissolved in 8 mL acetonitrile. Potassium carbonate (1.05 g, 7.6 mmol) and 1,4-dibromobutane (672 mg, 3.11 mmol) were added and the reaction mixture was refluxed overnight. The solvent was evaporated off. The residue was taken up in water and extracted three times with diethylether. The combined organic phases were dried on sodium sulfate, filtered and evaporated. Purification of the residue by flash chromatography on silica gel (dichloromethane/methanol/ammonia 1:0:0→140:10:1) yielded the title compound as a yellow oil (347 mg, 84%), MS: m/e=271.3 [(M+H)+].

출처