反応 #67699

反応方程式

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

収率 84.0%

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

収率 84.0%

溶媒

acetonitrile

反応条件

後処理

1. 1
   温度the reaction mixture was refluxed overnight
2. 2
   その他The solvent was evaporated off
3. 3
   抽出extracted three times with diethylether
4. 4
   その他The combined organic phases were dried on sodium sulfate
5. 5
   ろ過filtered
6. 6
   その他evaporated
7. 7
   その他Purification of the residue by flash chromatography on silica gel (dichloromethane/methanol/ammonia 1:0:0→140:10:1)

実験手順

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)+].

出典